


Can't Get Enough

by unholyseraphs (oncharredwings)



Category: Supernatural
Genre: Age Difference, Alternate Universe - College/University, Anal Fingering, Angst, BDSM, Daddy Issues, Daddy Kink, Dean in Panties, Dean's a quick shot, Dirty Talk, Dom/sub, Edging, Fluff, Forgiveness, Hand Jobs, Hurt/Comfort, M/M, Manipulation, Masturbation, Not Beta Read, Panty Kink, Praise Kink, Punishment, Spanking, Sub Drop, Sub!Dean, Sugar Daddy, Threesome, Trans!Sam, Voyeurism, bottom!Dean, curfews, dom!Cain, for a while, for a while lol, kept boy!Dean, paid relationship, please do not meet people off of craigslist to have sex lol pls, some unhealthy bdsm, swimmer!Dean, that's not healthy do not do this thank you, top!Cain
Language: English
Status: Completed
Published: 2015-02-01
Updated: 2015-02-11
Packaged: 2018-03-10 02:04:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 10
Words: 34,423
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3272768
Author URL: https://archiveofourown.org/users/oncharredwings/pseuds/unholyseraphs
Summary: <blockquote class="userstuff">
              <p>"Looking for swimmer" the ad starts out; the ad that changes Dean's life forever when he is sucked into the life of Cain Apidae, a rich CEO who just wants a bit of company. Dean does it for the money, but he doesn't realize how much he will come to love the lonely, mysterious man.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This is so self indulgent, I'm not even sorry.
> 
> Full title being: Can't Get Enough: AKA That Time When Dean Accidentally Became a Sugar Baby

Dean did not usually peruse personal ads, especially not the ones on Craigslist; they were too… _creepy_. But there was one ad in particular that had caught his eye.

 

**Looking for swimmer**

 

Dean dared to click on it, chewing on his bottom lip in curiosity. It wasn’t written like a lot of the ads were, in the stupid text shorthand; he _hated_ shorthand. It made everyone sound like idiotic fourteen year olds.

 

_Seeking male between the ages of 18 and 22; must be handsome, athletic, swimmer preferable. Will pay 1000$USD per month to live in apartment. Room and board covered; meals covered. Please call 312-844-8449 if interested._

 

Dean stared at the ad for what felt like an eternity before finally jumping to call the number; the ad itself was about a month old, so the guy could have easily filled the position by now. What guy _didn’t_ want to be paid one grand to live in an apartment? Of course, Dean assumed there would be sex involved, and while he did usually have a strict policy of _no cash for ass_ , he was a poor college student who would _gladly_ take one grand a month to fuck some (probably old) dude.

 

The phone rang a few times before a gruff voice picked up, “Hello.”

 

“Um, hi, um… Wow, I’m usually more articulate than this,” Dean paused to laugh a little, hoping the guy didn’t mind his awkward behavior, “but, I saw your ad on Craigslist and I thought I’d, um, call.” Silence answered him, so Dean jumped to speak again, “I mean, if you’ve already got a guy, I totally understand-.”

 

“What’s your name?”

 

“Dean.”

 

“And you swim?”

 

“Yes, Sir. I do.” Dean could feel his face heating up, realizing he’d called the guy _sir_ , mainly because he had a voice that elicited such respect. He sounded older, maybe a gruff military guy.

 

“How old are you?”

 

“Nineteen.”

 

“Hm.” There was the sound of pen scratching along paper, and Dean held his breath. Was this the interview? Was he being interviewed before being allowed to come by? He could have been making this all up for all this guy knew. “I would like to meet you, Dean.”

 

“Um, great, okay. When and where?” Dean asked, trying not to burst into a huge smile. _Bingo_.

 

“Do you know where The Abigail is?”

 

“Oh, yeah, I do. It’s the big fancy building near the university, right?”

 

“That’s right. Come inside, tell them Mr. Apidae is expecting you. They will direct you from there.”

 

Dean nodded, writing down the information so he didn’t forget. “Okay, cool. When am I coming by?”

 

“I assume you are a university student?” Mr. Apidae asked.

 

“Yeah, I am.”

 

“When are _you_ free?”

 

Dean leaned over to pick up his schedule off of his desk; it was only his second first semester and it was hard to keep track. “Um, I’ve got Friday afternoons off and all day on Tuesdays. And weekends I’m usually not too busy, unless I’ve got swim practice.”

 

“Tuesday would be fine. You may drop by between the hours of one and four in the afternoon. Do those work for you?” Mr. Apidae asked, sounding as if he were poised to write Dean’s affirmation down.

 

“Yes, Sir.”

 

“Good. I will see you Tuesday then.”

 

“Sounds awesome, Mr. Apidae.” Dean hung up first, smiling slightly to himself. It was probably foolish, going to some guy’s apartment for some weird sex interview, but he needed the money. Paying tuition was hard on a work study budget and his mother could only afford so much. Scholarships were helpful, but Dean still owed enough money to keep him constantly wavering on being discharged. One grand a month would be very helpful and if he could get his cost of living cared for? Dean would _gladly_ move off campus and save _that_ chunk of change from his tuition bill.

 

He tried not to be nervous, but when Tuesday rolled around, Dean could feel the knots in his stomach building early. After his roommate left for class, Dean woke up, showered, and stared at his closet helplessly. Was he supposed to dress up or down? Underwear or not? Probably not. He should have asked. _Stop being such a_ girl _, Winchester, and just get dressed. Jesus._

 

Dean rolled his eyes and snatched up his favorite AC/DC t-shirt and pulled it on over his head; it wasn’t super fitted, but it showed off his chest and waist. Paired with ripped up jeans that fit his ass nicely, Dean felt decent enough to start worrying on what to say when he arrived. Of course, he didn’t exactly _have_ the gig yet, and he wasn’t all that sure what it all entailed. Assuming Mr. Apidae would cover that in their meeting, Dean made sure his phone was charged, as well as carrying a knife with him. It wasn’t much, but it would be better than going in completely unarmed.

 

Half past noon, Dean left his dorm and trekked across campus and then down the sidewalk toward The Abigail. It was one of the fancier apartment buildings nearby that Dean would have sold his left kidney to live in. _Maybe now’s your chance. Minus the kidney thing._ When he reached the door and the doorman, Dean smiled, and introduced himself as Mr. Apidae’s guest. He was pointed to the elevator and told to press the _PH_ button.

 

“Penthouse,” he muttered. “No shit.” He hadn’t expected _that_. Of course, if the guy was going to be paying for his food, room, board, _plus_ one grand a month? Yeah, Dean should have expected a penthouse. The elevator ride up felt too short, but that was probably because he was even _more_ nervous now that it was almost time.

 

12:45.

 

Was he allowed to be fifteen minutes early? Dean decided to wait in the hall by the door until it was exactly one and then he went and knocked. The first knock did not prove to be fruitful, so he moved to knock again, just as the door opened. A man with dark gray hair and a full, trimmed beard stood in front of him, his brows seeming very serious. Dean felt his face turn red under the guy’s intense, blue eyes.

 

“Right on time. Good.” Mr. Apidae stepped aside and Dean slowly crossed the threshold, offering up his famous, cocky grin. “You are Dean, yes?”

 

He nodded. “That’s right, Sir.” Dean dared to take a look around and he could feel his jaw going slack. He had grown up in a poor farmhouse in Lawrence, Kansas. This was so far from that, he wasn’t sure what to do or say. “Shit,” he gasped.

 

“Hm. I take it, you are impressed?” Dean looked over at Mr. Apidae and nodded very slowly, feeling as if he could barely move his neck at all. “I am glad.”

 

“It’s _amazing_.”

 

The place smelled of something rich and expensive, like how he imagined Chanel No. 5 smelt or some Armani concoction. It reminded him of his freshman lit professor from the year previous, she’d always smelled of some name-brand perfume. Different shades of gray colored the walls and Dean took them all in, wondering if the guy had some _50 Shades_ complex. He almost laughed out loud, but he coughed into his hand instead, his eyes trailing along the fine grain of the hardwood floor. Nothing like the fake stuff he’d dealt with at home. The floor was so shiny in places, Dean could see his own reflection. He paused to remove his shoes and socks, not wanting to drag any dirt around the place; it was too fancy for him to muck up.

 

The living room was sunken down a few steps and Dean dared to walk down them, digging his toes into the creamy carpet. The fabric tickled the arches of his feet, but he continued to wriggle his toes anyway; it was soft, plush, and thick. He ran his fingers along the leather couch in comparison, feeling the cold fabric as his feet continued to spring from the warm carpet. It was a strange dichotomy. Leaving the living room behind, Dean walked down a hallway; there were no pictures on the walls, they were smooth and painted to perfection. They looked so perfect, Dean was afraid to touch them, in case his fingers left grease behind, so he kept his hands to himself, instead coming to stand in front of the pool.

 

The guy had asked for a swimmer specifically, but Dean hadn’t expected _this_ pool. It was large, bigger than he’d first expected. The water looked clean and the perfect shade of blue. Half of it was indoors, the rest outdoors, stretching along the large balcony outside. The entire back wall was made of glass, showing off the cityscape. Dean had never been a fan of the concrete jungle, even though he had come to Chicago to study, but from the height of the penthouse, Dean had a feeling he could come to appreciate the city a little more.

 

“Holy _shit_ , this is amazing.” Dean dared to walk over and kneel by the pool, touching his fingers to the water. It was warmer than he had expected. “Whoa, nice.”

 

“The water temperature may be adjusted to your liking.” Mr. Apidae followed him, his hands behind his back. Dean glanced up at him, his eyes roaming up from the rich loafers, the pressed, gray slacks, to the fitted suit jacket, waistcoat, and white dress shirt. The guy was sharp as hell; suddenly, Dean was reminded of ZZ Top’s song. _Every girl crazy ‘bout a sharp dressed man_ ; Dean had to agree.

 

“Sweet,” he said as he stood and pulled his shirt up over his head, letting it drop to the floor. “You mind?” When Mr. Apidae shook his head, Dean grinned and dropped his jeans to the floor, kicking them off to the side. For a moment, Dean stood naked in front of the guy before turning and diving in. The warm water enveloped him and Dean would have groaned if he hadn’t been under water.

 

Clearly, Mr. Apidae was content to watch Dean do laps, which he did until he had the courage to slip under the waterfall and go out under the sun. The weather was warm and the sun felt good on his skin. Dean grinned, slowly climbing out to go and peer over the balcony at the city. Chicago seemed so small from the height of the penthouse. It was amazing.

 

“You are very lovely,” Mr. Apidae told him, drawing Dean from his thoughts.

 

Dean turned around and winked. “Thanks, man. You’re sharp as hell, makes this even better.”

 

“I assume you wish to discuss the details of this.”

 

“Yeah. I do.” He licked his lips and became aware of his nudity, but since this was about sex, Dean decided to not care. He even allowed Mr. Apidae to enter his space. “So, I assume sex is a must, Mr. Apidae?”

 

“Call me, Cain.”

 

“Cain? Sure.” Dean nodded and blushed when Cain turned him around to check out his ass. Feeling cheeky (pun intended), Dean slid his hands to his ass and parted his cheeks to show off his hole. “Good?”

 

Cain made a noise that sounded pleased, but Dean couldn’t be sure. “Yes.”

 

“ _Awesome_. So, do I pass the physical?” he asked with a wink as he turned back around.

 

“I will not pressure you to have sex,” Cain said then, which surprised Dean. “If you do not wish to have sex, you are not required. All I ask is when you are here, you go as clothes-less as possible.”

 

“You want me to be in the nude?” Dean laughed and shrugged. “Why not? I hate pants anyway.”

 

“Good.” Cain gestured for Dean to follow him back inside, so he did, deciding to leave his clothes on the ground near the pool. Dean had a feeling he wouldn’t be needing them for a while. “The rules are simple,” Cain said as they came inside, “you live here, you mostly stay as you are now,” Cain glanced back at him hungrily, “and you do not have relations with anyone else. Not without my permission.”

 

Dean gave Cain the thumbs up. “I can be monogamous. No problem.”

 

“You will be paid on the first of each month, is that sufficient for you?” Cain asked as he reached for a checkbook. “You can also receive… bonuses.”

 

“Yeah? How do I do that?” Dean asked, walking over to stand near him, drinking in his scent; he smelled good, not too spicy or woodsy, it was something else. Softer? Dean had no idea what the guy’s cologne was, but it smelled fucking delicious.

 

Cain licked his lips. “How much do you enjoy self stimulation?”

 

“Jerkin’ it? Dude, I’m a nineteen year old guy, how much do you think I enjoy jerkin’ off?” Dean snorted and smiled. “Why? You like watchin’?”

 

“Yes,” Cain replied, completely deadpan.

 

“Right. Okay. So, if I jerk off for you… I get extra cash? Hey, I won’t say no to that.” Dean’s smile widened playfully. “So, um, look I gotta pay the university some money to move out, since I gotta break contract and all, um, how is that gonna work?”

 

“I will take care of it,” Cain replied as he handed over a check. “Here is your first payment, Dean. Your move in is immediate.”

 

“I got the gig? Hell yeah- I mean. Thanks.” Dean accepted the check. “You want me to get my stuff or…?”

 

“I have men to do that. All I need is your information.” Cain passed over a pad of paper and a pen for Dean to write on. “Our contract goes for three months.”

 

“That’s it?” Dean asked, feeling his stomach drop.

 

“It may go on longer if this works out, of course.” Cain half smiled, which was a first, but it didn’t reach his eyes. “You are welcome to any room in the apartment, I will have a key and photo ID issued for you in case you are stopped by the guards downstairs. Curfew is eleven, unless it is school related.”

 

A curfew? He hadn’t had a curfew since high school. Dean laughed but Cain’s face did not waver from _very serious_ , so he stopped with a blush. “Sure, eleven’s fine,” he mumbled, embarrassed.

 

“You may leave for class, of course, but I do ask, when you leave otherwise, you tell me where you are going. It’s common courtesy, Dean.” Cain accepted the pad of paper back. “I have to get myself to work, but, again, feel free to roam around. If you are hungry, the kitchen is fully stocked, or of course, you may order food. Put it on my tab.”

 

Once again, Dean gave Cain a thumbs up. “Thanks,” he said with his boyish smile. “When will I see you again?”

 

“I will be home by six.”

 

“Awesome… So, um, thanks?” Dean wasn’t sure what else to say; this was the oddest relation he’d ever had with a man. Cain nodded and then he was leaving, and Dean was left to look at the pool with a grin. “Best idea ever,” he muttered as he rushed to dive back in.

 

* * *

 

Cain returned right at six on the dot, it was almost uncanny, but Dean figured the guy was punctual. He just had that _air_ to him, the air of, ‘I am rich and I get shit done on time.’ Dean was camped out on the couch when Cain returned, munching on snacks, and watching TV, which was a damn good Tuesday spent in Dean’s opinion.

 

When Cain walked over to him, Dean looked up and muted the TV. “Yeah?” he asked. He’d put his shirt back on but that was only due to the fact that he’d gotten chilly. It had been stupid to not bring underwear, he’d realized in retrospect, but he’d remained naked otherwise. “You want me to take this off?” He gestured to the shirt.

 

“No,” Cain replied lightly. “You are enjoying yourself?”

 

“Huh? Oh, yeah, totally.” Dean nodded and popped more cookies into his mouth. He felt grossly fat for just eating cookies and watching TV, but he’d work it off later. “You want me to, um…” Dean trailed off and decided to make a few motions with his hand; hopefully that would be enough of a sign for ‘ _you want me to jerk my dick?_ ’

 

“When you are comfortable,” Cain replied as he sat down in a chair. Dean worried the guy would stare, but he didn’t, which was a relief. “Are you hungry? For more than just snacks, that is.”

 

“I’m nineteen, I’m always hungry,” Dean replied with a laugh. Cain nodded and stood up again, disappearing back toward the kitchen. Dean shoved another cookie into his mouth before getting up to follow, curious to know if the guy could cook or if he ordered out more than he bothered to use the fridge.

 

“What are your favorite foods?” Cain asked, a pad of paper in hand for notes. Damn, this guy really did want to keep him happy.

 

“Um… Pizza. Tacos. Pie - I _love_ pie… Chicken wings… steak. Bacon cheeseburgers. I’m sort of a garbage disposal, I eat basically anything you’re willing to feed me.” Dean shrugged and sat on a barstool at the counter.

 

Cain chuckled and set down the pad of paper. “I see, well, I have not had _pizza_ in years, I suppose tonight is a first for everything.”

 

“Dude, pizza is like… the best, cheap food you can order in.” Dean grinned excitedly. “I like meat supreme or whatever it is. My favorite.”

 

“I am sure you do.”

 

Dean balked; was that a pun? Had the guy just whipped out a sexual pun? He snorted and covered his mouth in embarrassment. “Sorry.”

 

“I will order us two pizzas… How about you… relax.” Cain picked up the phone and Dean took the hint, removing his shirt, and casually walking back to the couch, settling in with his legs open.

 

Dean listened to Cain order for a moment before wrapping a hand around his cock, stroking it slowly to life. He grunted at the little waves of pleasure forming; it’d been a while since he’d had a chance to rub one out, since his roommate was _always_ there… but now he was living the dream; getting paid to jerk off and be naked. It was the best gig he could dream up. Dean groaned as he slid his other hand under to cup his balls, rolling and rubbing them with his palm.

 

Cain appeared soon after, returning to his seat to watch. Dean looked over at him, trying to be sexy, but eventually he looked away, instead focusing on the ceiling and his inner fantasies. Dean let his mind roam to the grad T.A. in one of his classes; the guy was hot and Dean had had sex dreams about him more than once. He groaned again, using his precome to slick the ride, stroking faster. He cursed a few times, his toes curling as he grew closer; if he’d had lube, he would have started to finger himself, but that would have to wait.

 

“Son of a bitch,” Dean grunted, panting as he started to come. He gasped and groaned, thrusting his hips as he made a mess on his hand and stomach. “Shit- _shit_ -.”

 

Cain sat in silence, even after Dean finished, lying on the couch, sleepy and limp. Eventually, Cain stood and walked over to tilt his chin up. “You do not last long, we will work on it.” He wasn’t sure what to say to that.

 

 


	2. Chapter 2

“So, where do I sleep?” Dean asked timidly after he had cleaned up and they’d eaten their dinner. It was late, going on ten at night, and he had an eight a.m. class. He needed to get to bed or he’d never be able to drag his body out of bed.

 

“Follow me,” Cain replied as he stood up. Dean nodded and followed Cain up a set of stairs to the balcony that ran around the entire room. He was taken down a hallway where Cain opened up a black door to unveil a large bedroom that could have easily fit his dorm room several times over.

 

“Holy shit,” he whispered, pausing before stepping past the threshold. Cain walked over and opened up two more doors; one to a walk-in closet that would fit his clothes, his roommate’s clothes, his brother’s clothes, and probably his mother’s clothes and still have room over. The other door led to a bathroom that had a ridiculously large, glass shower and a deep set, jacuzzi tub. He had to hold back a moan at the idea of laying in that after a long ass day at school.

 

“Is this to your liking?” Cain asked. He walked over to hand Dean a remote. “This is for the television.” A button was pressed and Dean watched the flat screen appear from behind panels on the wall. HIs jaw dropped open and he could only nod weakly. “Wonderful. Now, you should get some sleep for your classes tomorrow.”

 

“Yeah- thanks…” Dean watched Cain leave him in the room. As soon as the door shut, Dean rushed over to jump onto the bed and moaned in the pillows; from the feel, it was memory foam. He grinned and rolled over onto his back, rubbing his stomach, and hips playfully.

 

Cain was paying _him_ to live the life of luxury; Dean started to laugh, grinning ear to ear. If anyone got the short stick of the deal, it was Cain, not him. He was going to live the high life and be paid to do so. Life could not get any better. It just couldn’t. Dean settled down eventually, his eyes growing too heavy to stay open, and soon he found himself wriggling under the covers, and snuggling into the pillow to sleep.

 

* * *

 

 “Winchester!”

 

Dean rolled his eyes at the sound of his ex-roommate’s voice. He pulled his collar up and kept walking; before he had risen for his class, men had let themselves into his room and deposited his belongings. They had scared the shit out of him, but he’d gone downstairs slowly, and found Cain was gone to work. He’d left him a note and there was breakfast in the oven, keeping warm. French toast, eggs, bacon, and sausage; it was the biggest meal he’d had for the first meal of the day in a long time. Better than campus food by a long shot.

 

“Dean! Wait up!”

 

Dean sighed and turned to face his roommate, waiting for him on the sidewalk. “Yeah?”

 

“Your stuff got… taken.. by scary dudes,” Ash panted as he took a few deep breaths. “What’s going on?”

 

“I’m moving out,” Dean replied with a shrug. “Got a job that pays good and includes room and board.” He turned and continued on down the sidewalk; it wasn’t really Ash’s business what had happened to him.

 

“ _Damn_ , are you serious? Sign me _up_!” Ash exclaimed as he followed Dean to the lecture hall. Dean rolled his eyes and kept walking. “So, can we still hang out?”

 

“Yeah, maybe,” he replied briskly over his shoulder before ducking into the building hurriedly. Ash was _so_ not cut out to be a kept boy; Dean had done some Google searching in his first class about kept boys, which was what he was now. Not that he wanted to be known as a prostitute, but it was a good deal, even if it was already starting to dig under his skin. How was he going to explain it to his mother?

 

 _You won’t. Don’t even tell her._ Dean sighed and sank into the back of the room with a yawn. Waking up before his alarm was starting to catch up with him. Of course, his mother would start to ask him how he was _paying_ for school, and he’d have to come up with an excuse, or maybe Cain would help him there.

 

“Hey, Dean,” Lisa said with a small fingerwave and smile.

 

Dean grinned and winked back. “Hey, Lis.”

 

“You coming to the party tonight?” she asked as she sank into the seat in front of him, leaning forward, making Dean’s eyes drop before jerking back up to her eyes. “It’s at the Theta Epsilon Nu house.”

 

“What time?” he asked, wondering if a sorority party was considered a “school function”. _Yeah right._

 

“Starts at ten,” she said with a smile that made his private parts hurt. “Hope to see you there.”

 

He returned her smile weakly and inwardly cursed. After classes were over, he had to hit the pool for swim practice, and then he’d go to the library to get his homework out of the way, and by then it’d be dinner time. Of course, he could always go back to the apartment for homework and dinner and _maybe_ convince Cain to let him go out for the evening. Parties were a part of the _social experience_ , and he was sure Cain wouldn’t want to _rob_ him of such things.

 

“I’ll be there,” he whispered to her as class started.

 

* * *

 

 Dean returned after swim practice, clothes damp and hair wet from the quick shower he’d used to rinse the chlorine from his skin. The apartment was quiet, so Dean walked over to the fridge to pull out some food to make a sandwich. One of the foods he could make _well_ were sandwiches. The door opened as soon as he took the first bite and he turned around, realizing he was still dressed. _Oops_.

 

“Dean,” Cain greeted as he walked in. “How was your day.”

 

“Isghoot,” Dean said around his bite with a thumbs up. He swallowed at the look on Cain’s face and managed to blush. “Sorry. It was good. How was _yours_?”

 

“Fine,” Cain said. He walked over to him to press a quick kiss to his cheek, which felt odd to Dean, but he didn’t want to comment on it either. “What do you wish for dinner?”

 

Dean shrugged and took another bite of sandwich. “I’m good for now,” he said after he’d swallowed the next bite. “You have something in mind?”

 

“I was debating on taking you to L’Antibes.”

 

He blinked a few times and swallowed the last bite of deliciousness. Cain stared at him expectantly so Dean finally broke the silence, “An-what?”

 

“L’Antibes, it is a French restaurant. You would, of course, need to wear something else, but I am sure we can put something together,” Cain said as he walked around Dean in a slow circle. “Clean you up a bit, you will do.”

 

Dean gulped and nodded. “Okay, uh, sure, we can do the… French thingy.”

 

“The _French thingy_ is one of the finest restaurants in this area,” Cain said firmly and Dean blushed. “Have you had French cuisine before, Dean?”

 

“Nope.”

 

“Well, you will enjoy it, as you say, you will eat _anything_ given to you.” Cain pressed his hand along Dean’s lower back and walked him toward the stairs go up to redress. “Do you own a jacket?”

 

“Like, a suit jacket?” Dean asked. “Um, I mean, I got one, but it’s too big and kinda dated, but-.”

 

“That is alright. It will do for tonight. I assume you own a button up?” Cain asked, his hand trailing feather light beneath Dean’s shirt to touch his skin; it made a shiver run down Dean’s spine. They were close together, up against the bedroom door. Dean looked up at Cain through his eyelashes, feeling hornier than he’d been a moment ago.

 

“Yeah,” he managed to gasp out. “I do.”

 

“Good.” Cain licked his lips and stepped back. “Slacks?”

 

“Um, I think so, yeah.” He nodded and then let himself into the bedroom, firmly shutting the door and trying not to groan out loud. Sure, Cain was hot, but he wasn’t usually Dean’s flavor, he was just in this for the money, but _damn_. The guy was making his thighs quake.

 

Shakily, Dean walked over to the closet, where all of his clothes were hanging; it looked so barren and it made him look like the poor white boy he was. It was a cruel reminder that without Cain, he’d be as poor as he had been yesterday. He pulled on the button up, which was a tad too small, but his jacket was too big, so he supposed it balanced itself out. The slacks were too long and he realized he had no dress shoes, so he just pulled on his converse since they were black (they weren’t even _real_ Converse, they were the knock offs). Dean spun to face the full length mirror on the closet door and sighed; he looked stupid, but that wasn’t his fault his closet was full of Goodwill shit he could afford on the fly.

 

Cain waited for him downstairs, checking his watch now and again. He expected the man to shake his head and tell him it was all a mistake and cut him loose, but Cain nodded and gestured for him to go on out. Dean blushed and walked down the hall toward the elevator with Cain on his heels. Dean stared at the floor, feeling his face continuing to heat up, the more he considered Cain and _him_ ; he had a feeling the old man could still fuck the absolute shit out of him and it was making Dean curious.

 

“You know how you said you wouldn’t force yourself on me?” Dean asked just as the door opened and they were going to the lobby, or they would have, if Cain hadn’t turned to look at him in surprise. “Well, I- I want to have sex.”

 

The smallest of smiles twitched along Cain’s lips and it even made his eyes sparkle just enough to make Dean blush again. “Good to know, Dean. Shall we?” Dean nodded Cain led him out to the front where a black car waited for them.

 

“Damn, you got a driver and everything? _Fan_ cy.” Dean smiled like a child in a candy shop as the door was opened and he climbed into the back. The seats were leather and Dean admired the stitching and the warmth as he settled in. Cain slid in beside him and after telling the driver where they were going, the partition was raised and Dean gasped when Cain’s lips went to his neck. The beard scratched his skin.

 

“Have I told you how handsome I find you?” Cain whispered, his voice low and husky. Dean moaned and shut his eyes when he felt Cain’s hands slide between his thighs, rubbing and massaging the muscles.

 

“Y-yeah, you told me,” Dean stammered, taking in a sharp breath through his nose. It wasn’t long before he was hard and Cain was rubbing and teasing him over the slacks. “Fuck-.” Dean grasped onto the handle of car door, breathing harder and faster with each teasing lick, kiss, and rub of Cain’s palm.

 

“Very beautiful boy,” Cain praised and Dean whimpered at the words; he loved praise. He could get off just on being told told how good he was in bed. “But, I suppose, I should wait until we arrive to eat before letting you come.”

 

Dean gulped. “W-what?” Cain chuckled and stroked Dean’s hair with light touches, which only made made goosebumps rise along Dean’s skin again.

 

“I told you, we would have to work on your stamina. I like my boys to _last_. You may not come until I tell you, am I understood?” Cain asked quietly, his mouth right against Dean’s ear. Dean nodded several times in a row as he stared out the window. “Answer me, Dean. WIth your voice.”

 

“Yes, Sir,” he managed to say, even though his voice was close to cracking with anticipation. He’d never known himself to be so aroused by commands and deep voices, but he _was_ so fucking horny. His lips and throat felt dry, but before Cain’s hands could work him up any further, they were pulling up in front of the restaurant.

 

“Ah, we’re here, fantastic.” Cain kissed him before the door was opened and Dean had to take a few deep breaths to calm down and regain control of his body. His lips felt swollen and his mouth felt fucked, as if Cain had shoved his dick down his throat.

 

Cain turned and offered his hand. “Coming, Dean?” He gulped at the innuendo and allowed Cain to lead him into the restaurant. People stared at him, looking him over, but the woman at the front desk dove right into French and Dean panicked; did he have to know French to eat here?

 

“ _Bonsoir Monsieur, que deux ce soir_?” she asked and Cain smiled.

 

“ _Oui_.”

 

“ _Ah, bon! Suivez-moi , je vais vous prendre à votre table habituelle._ ”

 

Dean pretended to understand whilst smiling and nodding, but the more they ventured into the fancy restaurant, the more nervous and out of place he felt. He wasn’t exactly Mr. Silverspoon, he was definitely from the opposite end of the tracks. Back home’s idea of a fancy restaurant involved plaid tablecloths and deep fried chicken. The extent he had of French food were French fries, and he was fairly certain that was an American concoction.

 

Cain exchanged more words with the hostess before they were seated, and Dean was handed a menu with words he didn’t understand and the restaurant was _so_ fancy there weren’t prices on the menu; if you had to ask, you couldn’t afford it, Dean assumed. He glanced over the menu and then glanced up at Cain more than once, wondering if this were a _usual_ for the guy, or if this was Cain attempting to impress him.

 

“Just so you know, you don’t gotta spend a buttload of cash on food for me, I’m already impressed with the apartment,” he said quietly, not wanting to offend anyone nearby, which there weren’t _many_. It was quiet and they were mostly in private. He had a feeling Cain did that for a reason.

 

Cain chuckled. “Pick out what you wish to eat, Dean.”

 

“I can’t even pronounce this stuff, let alone know what it is,” he said, feeling extremely uncultured and uneducated. “Look, I’m from the sticks, okay? We ain’t got no fancy learnin’ out there.”

 

Cain set his menu aside. “If you wish to eat elsewhere, I suppose we may do so.”

 

“It’s just- I don’t want you to think you gotta wine and dine me like you’re gonna teach me something new and fancy. I’m not a charity case, okay?” Dean glanced back down at the menu and hid behind it; he suddenly felt like Julia Roberts in _Pretty Woman_ (okay, so yeah, he watched it _once_ ).

 

“I am not attempting to culture you,” Cain replied. “If you are truly uncomfortable, I will not subject you to this… However, I do suggest you try something here, the food is to die for… The dessert menu is rather extensive.”

 

Dean glanced up warily; Cain already knew how to persuade him, it was a little scary. “‘Kay.” Cain smiled at him and Dean dropped his eyes back to the menu. “So, we get like… lots of food, right? I-.” Dean cut off when the waiter appeared.

 

“Good evening, Sir,” the man said to Cain, his accent thick. “I see you have brought a special someone with you.”

 

“Yes,” Cain said with a fond smile. Seriously, the guy had to stop making him blush so damn much. “I have. We will start with-.” Cain paused. “You are not old enough to drink, I almost forgot… Forget the wine.” Cain waved his hand quickly.

 

“Ah, I see, shall I suggest something else to drink, Sir?” the waiter asked.

 

“Bring us water, it will keep the palate clean,” Cain replied and the man bustled away to do as was asked of him. “Have you decided. The duck is quite good.”

 

Dean shrugged and set the menu aside. “You pick,” he said. “I don’t trust my judgement at a place where I can’t pronounce the food names.”

 

“Ah, well then, I will do my best to pair you with something I believe you will enjoy.” When the waiter returned, Cain dove into ordering for himself first, and then for Dean. “As for my… special someone,” Cain said with a smirk, which Dean couldn’t decide was a good smirk or not, “he will have for the first course the cherry and apple wood smoked bay of fundy salmon, the creme fraiche, and brioche crouton course. For the second course, he will have the… _special_.”

 

Dean blinked. What did that mean? It didn’t sound like it was something he would be excited about, but Dean had no choice but to smile and nod when the waiter glanced at him. The menus were handed over and then Cain’s attention was back on him. “The fuck is the _special_?” he asked, probably too loud.

 

“Language, Dean, we are in a dignified restaurant,” Cain replied.

 

“ _Well_?”

 

“You will like it, I promise.”

 

“The guy looked at me like I grew two heads when you said that. DId you just tell them I wanted spotted cock or somethin’?”

 

“It’s spotted _dick_ , Dean, and that is an English cuisine, not French.” Cain sighed and Dean wondered if he were wearing on the old man.

 

 _Probably, you’re about as cultured as the chairs… the chairs are probably more cultured than you._ “Sorry,” he replied with a shrug. “Seriously. What is the special?”

 

“It is a surprise,” Cain replied with a shrug. “But, I ask that you try the first course, I really do think you will enjoy it.”

 

“I’ll try it,” Dean agreed. When the followed, his mind turned to Cain telling him when to come. He had no idea how _that_ would work here, but he wasn’t sure he wanted to know either. “Can I ask, why me?”

 

“What do you mean?”

 

“I mean, I’m sure you got lots of responses, so why me?” Dean shrugged and picked at his jacket. “I’m sure there were other contenders.”

 

“There were several, yes,” Cain agreed with a nod, “but none of them had your spark.”

 

“Oh.”

 

“I know you are probably only doing this for the money,” Cain said and the words made Dean’s stomach drop; it was awkward to be called out so soon. “However, I do hope you at least enjoy your time with me.”

 

“Dude, you let me masturbate, swim, walk around naked, you feed me, and I’ve got a memory foam mattress. I’m set up for enjoying myself at least a few times.” He winked and it was satisfying to see Cain look bashful for half of a moment. “You don’t gotta try so hard, ya know.”

 

“I beg your pardon?”

 

“I mean, with all the fancy stuff, you don’t gotta try so hard to keep me.” He shrugged. “I’m set. Really.”

 

“Hm.” That was the end of the conversation and Dean glanced down at the tablecloth again; he had a feeling Cain was a man of few words, which always made dinner dates _awkward_ in Dean’s opinion.

 

Mercifully, the first course arrived, and Dean dug in hungrily. Cain was right, the food _was_ good, if not a little strange and not something he was used to. Still good. His mother would have been proud of him, eating in a fancy restaurant, and consuming weird ass food. He grinned at the thought, but then remembered he couldn’t tell her, and the smile fell away, so, he just shoveled more food in. He was done long before Cain, which made Dean wonder if he’d eaten too fast. Did fancy people eat slow on purpose?

 

“That was good,” he said with a belch which made his eyes widen. Cain continued to say nothing, so Dean gave up, and looked around the room. “Where is everyone?”

 

“I always ask for privacy,” Cain replied then, making Dean jump; he hadn’t expected an answer.

 

“Right. Okay, cool.”

 

The quiet continued, until the second course arrived and Dean had to do a doubletake. Whereas Cain’s plate was some type of fish, Dean’s plate was… a bacon cheeseburger. He stared with wide eyes, as the thing was lowered in front of him; it looked so fancy with its little brioche bun and parsley or something next to it. There was even a little handful of fries to go along with it. The waiter looked disgusted but Dean drew his eyes up from the food to Cain’s smarmy grin.

 

“No fucking way,” he laughed with a boyish smile. Dean felt like a child again; it was wonderful. “You got a fancy ass restaurant with snooty French people to make me a fucking bacon cheeseburger. Dude, you are somethin’ else. Thanks.” Dean plopped the bun on top of the bacon and chowed down eagerly. Even though the French had some weird food, Dean had to admit, they made _damn_ good burgers. He groaned more than once, practically having a food orgasm. Cain made no comment and Dean was glad the guy wasn’t telling him to shut up, because it would have been impossible.

 

Dinner disappeared faster the second time around and then Cain ordered them dessert. Dean almost groaned in protest, but he had to try French dessert; he believed Cain on the dessert thing. Tired, Dean leaned back against his chair and slouched, only sitting up when Cain slid his chair closer.

 

“Uh, hey, sorry- I know, I know. Sit up.” He rolled his eyes and attempted to do so. Cain leaned in and kissed his neck again; it was such a small and intimate gesture, it had Dean’s immediate attention.

 

“Remember what I told you earlier,” Cain warned him quietly as his hand cupped Dean’s crotch, squeezing and rubbing him to hard.

 

“Right here?” Dean whimpered, biting his lip as Cain worked him slowly, not even bothering to put his hand down his pants. Cain was going to make him come in his underwear like he was a teenager again.

 

“Right here.”

 

He took in a few deep breaths and stared at the door the waiter kept appearing from; what if the guy caught them? Or did Cain have a standing thing about himself and his pretty boys? Dean had a feeling he wasn’t the first boy to be brought here for a handy. He grunted a little when Cain rubbed his bulge in quick circles, gripping and stroking him through the slacks. A droplet of perspiration worked its way down Dean’s spine, making him shiver; he was soon highly aware of how much he was beginning to sweat and breathe harder.

 

“Relax,” Cain said in his ear. “No one is going to bother us.”

 

“Dude, we’re in a- _ahh…_ restaurant.” Dean shifted, feeling his hips try and press back into Cain’s hand. It was embarrassing how much of an eager slut he could be. “Someone is gonna- se-.. _seeeefuck_.” He shut his eyes; his cock was aching and making a wet mess in his underwear. “I’m about to-.”

 

“Did I say you could come?” Cain asked quietly. Dean shook his head. “Then, don’t.”

 

“I don’t think I can hold it,” he whined, his hands gripping the edge of the table so hard his knuckles were white and the bones stood taut against his skin. “I’m serious, I’m about to blow-.”

 

Cain made a noise; Dean wasn’t sure what it meant, but it didn’t sound happy. He whined and felt his body give in, coming thickly in his underwear and pants. A blush filled his face as he imagined the mess getting everywhere, even if he knew it was somewhat contained; he just hoped his slacks didn’t stain. The waiter returned soon after and Cain moved back to his side of the table. Dean didn’t miss the look of disappointment.

 

 

The ride back to the apartment felt awkward and stifled. Dean stared out the window, feeling bad and needing a shower. Cain’s silence stretched all the way into the apartment; it wasn’t until they were inside that the man decided to speak again.

 

“I hope you enjoyed your meal,” Cain said, which Dean assumed an attempt to reconcile the awkward.

 

“I did,” he agreed with a shrug, removing his jacket and shirt; not because he knew the rule was he had to be nude, but because he didn’t want to be in the sweaty clothes anymore. “Sorry I suck.”

 

Cain tsked. “I apologize, Dean, I do not mean to make you feel bad about yourself. You were very good this evening. Very well behaved.”

 

A blush creeped up Dean’s neck and along his cheeks. “Oh… okay… good, I guess.” He dropped his slacks and sticky boxers. He couldn’t look Cain in the eye, not even when Cain walked over and cupped his cheek.

 

“Dean, look at me. Please.” Dean finally raised his eyes to look up into Cain’s blues. “You were very good tonight, I do not regret asking you to be the boy I bring out with me.”

 

Dean chewed on his bottom lip and wondered if this would be a ticket to the party. “Since I was so good, can I go to a… school function tonight? It’s at ten and I know curfew is eleven, but it’d be cool if you extended it tonight.”

 

“A… school function, hm?” Cain asked. “I suppose if it is a _school_ function, you are permitted to go.”

 

Dean smiled brightly. “Thanks. I gotta shower and get ready-.”

 

“Dean.”

 

“Yeah?”

 

“Be home by no later than three.” Cain pointed a finger at him and Dean nodded as he rushed upstairs to prepare for his “school function”.

 

**Notes for the Chapter:**

> the french is from google translate, so sue me


	3. Chapter 3

The door clicked as softly as Dean could make it, flinching at even the slightest sound. Carefully, Dean turned on his heel and walked back toward the stairs, almost having a heart attack when Cain addressed him.

 

“It’s five thirty in the morning. I told you to be home by three.” Cain’s voice was… toneless, but not _monotone_. He sounded as if he were guarding his emotions and feelings; it was an odd tone to hear.

 

“I’m really sorry,” Dean said, walking over to be reprimanded. He kept his eyes on the floor, folding his hands in front of his body. “I didn’t mean to stay out so late, it was just… a really… wild… school function.”

 

“We both know you were at a party, Dean, you may as well be _honest_.” Cain stood up and straightened his jacket. Dean trailed his eyes up Cain’s form; red, leather shoes worked oddly well with the olive green, plaid suit; a light purple shirt and olive tie topped off the outfit. Five-thirty in the morning and the guy was already dapper as fuck.

 

“It was a wild party, I shouldn’t have stayed out so late, I’m very sorry. It won’t happen again.” Dean flinched and tried to make himself smaller. He didn’t like being punished; it reminded him of his father.

 

“I am _very_ disappointed in you, Dean,” Cain snapped, his voice ice cold. “I expected you to misbehave, yes, you are nineteen and young men are not well disciplined.. but I did expect you to come home on time.”

 

Dean swallowed a goose egg forming in his throat as his eyes started to sting; he angrily tried to blink the tears away but they were misting over and he wasn’t sure if it were a result of being a little drunk. Being told someone was disappointed in him cut to the quick; it hurt more than being slapped. “I’m sorry,” he said again, unable to say anything else, his voice barely a whisper.

 

The mood of the room shifted and Cain reached over to shift his chin up, his hands gentle, and when he spoke again, the clipped tone was gone. “But, I can forgive you.”

 

Dean blushed and nodded, still attempting to not cry, but his eyes were leaking, and his jaw was starting to tremble. “I didn’t mean to-.” He cut off to take a breath. “Disappoint you.”

 

“I know,” Cain said quietly. “Despite your forgiveness, I still must _punish_ you, I hope you understand.”

 

“Punish?” Dean raised an eyebrow. Was Cain going to _ground_ him? He hadn’t been grounded since the tenth grade.

 

“Yes. Punish.”

 

* * *

 

 Dean screamed into the pillow when the paddle struck his already sore, red ass again. It hurt and it felt good; he was confused by his erection and by the fact that he kept whining and whimpering, wanting to be spanked _more_. He had watched a chick get spanked once on the internet, but he’d never imagined being into it. But he was panting, sweating, and his cock was dripping dangerously the more Cain spanked him.

 

Dean decided he _liked_ punishment.

 

“One more,” Cain told him and Dean winced when the paddle struck his ass one last time. “I would punish you more, but I do not wish to send you to class in agony.” Dean gulped and allowed his body to sink onto the bed; he’d forgotten about class completely.

 

“I don’t think I can go to class,” he mumbled into the bed, but the door was opening and shutting. Great, Cain was going to leave him to figure his confusion out on his own. He sighed, moving to get up, but his body ached, and his ass tingled from being red and sore. Dean jumped when Cain returned and then a soothing lotion was being rubbed onto his cheeks; he flushed and tried to twist and look at him.

 

“What are you doing?” he asked.

 

“Taking care of you,” Cain replied. He looked up at Dean, very serious. “If a man or woman ever dominates you and then does not care for you after, you leave them. Do you understand?” Dean nodded slowly. “Good… It always in a dom’s best interest to care for their sub after everything they do together.”

 

“Okay.” Dean had no idea what any of those things meant but he was just going to go along with it. “Sounds… good to me… That feels nice, by the way.”

 

“Good. Now, I realize you are tired and hungover.” Cain set the lotion aside. “That does not mean you can skip class. Get ready. Now.”

 

He groaned but nodded his agreement. Cain left him to dress, which Dean did gingerly, trying to find his softest pair of boxers; he was in desperate need of new underwear. Sitting through lecture was _not_ going to be fun.

 

* * *

 

Sitting through lecture was not fun.

 

Not because his ass hurt (which it did) but because he couldn’t stop thinking about Cain spanking him. The more he thought on it, the hornier and desperate he became. Eventually, Dean couldn’t take it anymore and he fled the lecture hall to the closest restroom, deciding to give a little payback.

 

The restroom was empty, so Dean locked himself in the largest stall, and dropped his pants and boxers, stroking his cock quickly to being hard. Holding back moans by biting his lip, Dean held his phone carefully and snapped a photo of his cock, sending it to Cain. Of course, that didn’t guarantee the old man knew how to work picture messages, but he would go on blind faith and say he wasn’t _that_ behind the times. Dean grunted and took a quick video stroking his dick; Cain _did_ tell him he would get extra cash for masturbation.

 

Who gave a shit where he did it as long as Cain got to see the byproduct?

 

Dean grinned and took a selfie, which he wasn’t sure if it were sexy or goofy, but he sent it anyway. After, Dean returned to jerking it, groaning, and uncaring who heard him. He wanted Cain to punish him again, to spank his ass harder. Breathing heavily, Dean decided to text Cain too. Because why not add to the madness?

 

- _i want u to fuck me_

_and i want u to spank my ass again_

 

Dean swallowed and sped up his hand, trying to hold on longer this time; Cain was right, he needed to learn how to edge. The sound of his phone buzzing made him jump and almost come, but he held back, checking his messages.

 

**Are you being bad?**

 

- _yes. real bad. jerking it in the bathroom @ school_

 

**I am at work, Dean.**

 

- _good. get hard old man. you make me fucking hard. i hate u._

 

The next message didn’t come for a few more minutes. Dean continued to stroke his cock, groaning, and whimpering as he grew closer, forcing himself to hold back.

 

**When is your last class?**

 

_-done at 3:30_

 

**When you get home, you are to wait in front by the door, on your knees. Naked. Do not touch yourself, am I understood?**

 

Dean blushed and gasped, finally coming, on his hand and on his phone. “Shit-.” He sighed, letting himself go, trying to type through the mess.

 

- _yes sir._

 

**Good.**

 

A ghost of a smile flitted across Dean’s face before he cleaned himself and his phone up to go back to class. Unfortunately, he still couldn’t focus.

 

 

Hardwood floors were extremely uncomfortable after fifteen minutes let alone after an entire hour. His knees ached so badly, Dean had a feeling he wouldn’t be able to kneel on the floor much longer. He sighed, growing restless, but then the door unlocked, and he froze, wanting to be good. He’d already misbehaved today, he had to make sure to do _something_ right. Cain walked in shortly after the door unlocked and there was a pleased smile on his face; his smiles were never large, but Dean liked them. They felt private, special.

 

“Very good,” Cain praised, walking over to run his hand through Dean’s hair. He looked up at Cain, trying to look cute and innocent. “I almost want to forgive you for making my meeting with Portugal very uncomfortable.”

 

Dean smiled, pleased with himself. “Leave it to me.”

 

“Hrm.” Cain walked away, leaving him in the front room. “Come here, Dean.”

 

“Yes, Sir.” He stood up and eagerly followed, glad to stand up, feeling his knees stretch and ache. Cain went to sit on the couch and Dean followed, unsure of what was about to happen. “Am I still in trouble?”

 

“Oh, yes.” Cain patted his lap. “Lay down.”

 

Dean smiled and then quickly cleared it away; he wasn’t supposed to be excited about being in trouble. “Yes, Sir.”

 

Cain provided a pillow for his head, which was nice of him, Dean figured. He stretched out on Cain’s lap and the couch, surprised when he felt Cain’s hand rub his cheeks tenderly first. Was this an apology before the punishment? Or was it just admiration? He took a deep breath and held it, until four smacks were put on him in quick succession; the breath whooshed out of his lungs and he pressed his forehead into the pillow as tears stung his eyes. His body was still sore from earlier.

 

“You should know better than to send dirty pictures while I am at work,” Cain said casually, going back to rubbing the soreness away. “Could have gotten me in trouble, Dean Winchester.”

 

“Sorry,” Dean gasped, swallowing before he drooled on himself.

 

“No, you are not. Not yet.” Cain smirked and spanked Dean again. “But you will be.”

 

Dean groaned, his cock hardening against Cain’s lap. The things that turned him on lately were really freaking him out, but he decided to go with it; he was young, weird shit happened in your twenties. “I am!” he cried, turning into a whimper when his ass was spanked again five times.

 

The flesh felt hot and sore. Dean had a feeling his entire ass was completely red. Cain made a pleased noise and Dean licked his lips. His heart was about to fly out of his chest any minute.

 

“Your freckles look nice on your red ass,” Cain commented, which made Dean’s back turn red from embarrassment. “Ah, yes, look at your little constellations.” Fingertips traced his freckles as they stood out like leopard spots. Dean shivered.

 

“I need water,” he whispered, swallowing at nothing. “Please.”

 

Cain rubbed his ass again before carefully shifting their bodies. Dean allowed Cain to lie him face down on the couch, and Dean tried to calm himself down. The spanking was good, but he was growing anxious; his heart rate kept climbing and he felt horribly dehydrated. Maybe he should have eaten something before waiting in the front room for Cain like he was told to. When Cain returned, he knelt down on the floor beside him, and helped him sip water, and rubbed his back in circles. Why the fuck was he so damn sad all of a sudden?

 

“I’m sorry,” he whispered, this time really meaning it. Cain nodded. “I don’t know what’s wrong with me.”

 

“I know you’re sorry, it’s alright.” Cain continued to rub Dean’s back, soothing him gently. “I’m not angry, Dean. I find your defiance endearing. That _spark_ I was talking about earlier.”

 

Dean nodded, sipping more water sleepily. “I’m tired.”

 

“You’ve had a lot today, you were _very_ good.” Cain smiled and pressed a kiss to Dean’s shoulder. “Do you wish to sleep here or I can carry you to your room?”

 

“I’ll stay here for now. I feel really sore.”

 

“I will go get you something to take for the pain.” Cain kissed his shoulder again and then left to do as he said. Dean relaxed into the couch, burying his face in the cushion. It smelled faintly of Cain; that expensive scent. It made Dean’s loins ache, but he was too tired to do anything about it. Cain returned with the Tylenol, and then a blanket was laid over his back.

 

“Sleep, Dean,” Cain whispered in his ear, his lips brushing his temple. “I will be here when you get up.”

 

Dean nodded and he couldn’t even respond before sleep was making him its total and complete bitch.

 

* * *

 

Dean jerked awake from a nightmare; he fell asleep with his heart racing and woke up with it doing the same thing. Cold sweat made him shiver and he sat up, pulling the blanket over his body, since it had fallen to the floor. The apartment was dark and quiet, and Dean could make out through bleary vision the clock read half past two in the morning. He turned his eyes to the stairs and carefully began to walk over to them.

 

Returning to his room would have been the smart thing, but Dean went to stand outside of Cain’s door. He stared at it, hugging the blanket to his cold body. The desire to knock grew so feverish, he finally decided to go with it; he knocked on the door and waited. He’d been at Cain’s for three days and he was already wanting to cuddle up to the guy like a tiny puppy?

 

_What the fuck is wrong with you. Jesus, Dean._

 

He sighed and knocked again, really wanting Cain to answer. The door finally creaked open and Dean spat out the words quickly, “You promised you’d be there when I woke up. You weren’t there.”

 

Cain’s face softened and he stepped aside, letting Dean into his bedroom. If he’d been in less of cuddling needs, Dean would have admired the vastness of the room, but instead, he walked over to the bed and climbed on top of it. Cain joined him and then Dean was right in the man’s side, trying to burrow into his ribcage.

 

“Something wrong, Dean?” Cain asked, even as his arm wrapped around Dean’s shoulders tentatively.

 

“Had a nightmare,” he replied gruffly. Admitting that he needed cuddling was not exactly his usual MO, but it felt necessary after the awful dream. “‘bout my Dad. He was a son of a bitch.”

 

“Was?” Cain asked.

 

“He died. Heart attack… But, he was awful to me. All the time. Always pickin’ on me, sayin’ I wasn’t… good enough and shit.” Dean stared at the clock next to Cain’s bed, lying his head on Cain’s chest timidly. He hoped Cain didn’t mind the sudden intimacy. “I’m sorry, I’m gettin’ all up in your space.” Dean went to pull away but Cain’s arm tightened around him, so he relaxed.

 

“I do not mind,” Cain replied, rubbing Dean’s back again. “I should have carried you to bed when I went, I apologize.”

 

“It’s okay.”

 

“But you were telling me about your father.”

 

He sighed heavily. “Ain’t much else to say. Guy was a douche canoe and I always get shitty dreams about him beatin’ me up. I can never escape him. It sucks.”

 

“I am sure Freud would have much to say on this matter,” Cain said. Dean frowned, almost asking _who_ , but he vaguely remembered some psych class somewhere about the guy.

 

“Freud was the dude into the kiddie love, right? He was all about how sons want to bang their moms and daughters vice versa?”

 

“In more or less words, yes.”

 

“Fuckin’ weirdo,” Dean mumbled darkly. “But, yeah, I’m sure he’d go on and on for days about me.”

 

Cain didn’t say anything for a moment, but when he spoke again, it made Dean’s world halt. “Dean, if I ever say or do something that truly upsets you, I want you to tell me. I never want to make you feel uncomfortable, nor do I want to ever upset you. I care for your well-being.”

 

“You don’t even know me,” Dean whispered.

 

“That does not mean I cannot care for you.”

 

Tears.

 

They were falling so fast, he couldn’t stop them. Cain was surprised but so was Dean. He tried to tell Cain that it wasn’t him, but he couldn’t get the words out. He just kept on crying. Eventually, Cain gave up on trying to ask and simply held him tightly. Dean wanted to tell Cain that it wasn’t _him_ upsetting Dean; it was the idea that a man who had known him for three days cared more for him than the father he had known for seventeen years ever had.

 

The tears subsided after Dean felt too tired to cry, but Cain continued to hold on. He realized that he had no desire to return to his own room, so Dean settled into Cain’s bed like he belonged there. Cain didn’t seem to mind either.

 

“Good night, Dean.” Cain pressed an affectionate kiss to his forehead and he blushed with a warm smile at the feeling. It was a nice feeling.

 

“Good night, Cain,” he whispered back.

 

 


	4. Chapter 4

In the morning, Dean was too tired, sore, and emotionally drained to go to class. He stayed in bed most of the day, only getting up to pee and find a snack when his stomach would no longer be ignored. The days blurred so badly he wasn’t even sure what day it was or if he needed to go to swim practice, so he texted his coach to tell him he wasn’t feeling well. Dean munched on chips and made his way to the sunlit balcony, staring at the pool water for a moment.

 

A brief thought on how easy it would be to drown flashed through his mind before he rolled his eyes and told himself to stop being so damn melodramatic. This was not a Lifetime movie. Setting the bag of chips down, Dean went to the deepest end and dove into the pool, relishing in the shock of cool water, staying under until he needed to break for air, bursting to the top with a welcomed gasp.

 

Lungs expanded to the point of wanting to burst out from behind his ribcage and then Dean allowed them to deflate into tiny sacs of nothing. After, he relaxed and breathed normal, starting to do laps. Even though he had no emotional and mental energy to go to class and practice, that wouldn't stop him from using the pool here. That’s what it was for, wasn’t it? Plus, the sun felt good on his skin, in comparison to the way the lights would feel if he went to school to swim. This was better. Plus, after, he could relax on a lounge chair and stare at the city while he tanned.

 

“Enjoying yourself?”

 

Dean startled. “Jesus Christ! Make a noise next time, man.” Dean took another deep breath to calm his heart. “Jerk.” Annoyed, Dean swam over to the pool’s edge and rested there, looking up at Cain. “Why aren’t you at work?”

 

“I got off early,” Cain replied with a shrug. He sat down in the chair opposite Dean. “How are you this morning?”

 

“Tired, didn’t go to class obviously, but I figure I should do laps to stay in shape.”

 

Cain half smirked. “Please, don’t let me stop you.”

 

“You just want to watch me swim naked.” Cain shrugged and Dean laughed. “I mean, I don’t _blame_ you. I do look fabulous naked.”

 

“Speaking of, I have a gift for you,” Cain said suddenly, which piqued Dean’s interest. A gift? What had he done to earn a gift?

 

“A present? I like presents.” Pressing his palms into the ground, Dean hauled himself up out of the pool, and started to walk back toward the house, snatching up a sun warmed towel to dry off in, so he didn’t drip water all over the floor.

 

True to his word, there was a bag sitting on the counter. Dean smiled and walked up to it, eagerly reaching inside; he felt like a child at Christmas, but this was the first time he’d had a significant other buy him a gift. That thought made him pause. Did he consider Cain a significant other? He shook his head and decided not to think about it, instead unveiling the tissue paper and letting it sidle to the ground sadly. Inside the bag was something he hadn’t expected; he’d assumed Cain had bought him some sort of sex toy, since that was what this was all about, but what he held in his hands was definitely not a sex toy.

 

Dean spun around to face Cain in surprise. “Um, dude, this is like… not, um, for guys.”

 

Hot pink satin and black lace panties; that was what he held in hand. The black lace would cover the majority of his butt, and wrap around his middle and thighs, but Dean was certain Little Dean and Friends would not fit inside the skimpy fabric. There was no way; he wasn’t _that_ small. Did Cain think he was small?

 

“They can be for whomever wishes to wear them,” Cain replied as he came inside. “I do not believe in gendered clothing. Clothing is simply that; it need not be gendered.”

 

Dean’s eyes dropped down to the panties in his hand, but Cain’s words made him think on Sam, who was always struggling with himself and what he liked to wear and what he wanted to be. Dean had grown up with Sam being a gangly, awkward _boy_ , but his mother had called him last year, telling him that Sam saw himself as unsure of what and who he wanted to be, but it was still okay to call him ‘he’. That hadn’t stopped Sam from showing up on a visit with his mom, with his hair long past his shoulders, up in a high ponytail, and wearing a dress. The words struck a little too close to home.

 

“Dean?”

 

“Yeah?” Dean set the panties back in the bag.

 

“You went away for a moment there,” Cain said, stepping closer to him. “Are you alright?”

 

“Yeah. I’m fine.” Dean nodded; he wasn’t about to give up the details about his brother to a man he hardly knew. They weren’t his secrets to tell. “Sorry, I just got thrown off is all.”

 

“You do not have to wear them,” Cain said slowly. “But I would appreciate it if you did.”

 

Dean rolled his eyes, wanting to snap at Cain for his manipulative bullshit, but he knew he was just angry because his father would have beat the snot out of him if he’d wanted to wear girly underwear. But Dean held back the thoughts and snatched the panties out of the bag, stepping into them.

 

“They won’t fit,” he said firmly as he yanked them up. Immediately, Dean ate his words, because they _did_ fit, and they didn’t just fit, they were comfortable too. “Shit.”

 

Cain chuckled and Dean gave him a dark glare. Cain held up his hands in his own defense. “They look very nice on you.”

 

Dean grumbled and blushed, trying to twist to view his butt. “How the fuck are the twins even fittin’ in here, it’s like witchcraft.”

 

“Ah, the wonders of spandex.” Cain closed the distance between them and tilted his chin up for a kiss. Dean whimpered and chased his mouth when Cain pulled away; he liked kisses and affection. They were like drugs. “Needy today, are we?”

 

Dean blushed and pulled back. “I’m sorry-.”

 

“Never be sorry for wanting to be wanted,” Cain said firmly, cupping Dean’s face in both hands for another kiss. “I left work early for you, and I know that doesn’t mean much to you, but I promise, it means the world.”

 

Dean smiled shyly. “Oh… Okay.”

 

“This weekend I wish to take you to my cabin.”

 

“You have a cabin? Sweet.”

 

Cain nodded, petting Dean’s hair affectionately. “Do you wish to go?”

 

“Hell yeah, I love campin’ and outdoor shit. I’m all about that.” Dean nodded. “I’ll even model these for you in the woods.” He turned even redder at the admission. “I don’t know where that came from.”

 

“Don’t question it too much.”

 

“So… What day is it, I don’t even know.”

 

“Friday. I suggest you get ready to go out, if we can, I’ll drive us up tonight.” Cain spanked Dean’s butt once lightly. “Go pack.”

 

Dean grinned and dashed away not even caring that Cain was _definitely_ checking out his ass the whole way.

 

* * *

 

The cabin was in Wisconsin, so the drive was longer than Dean had expected, but he slept most of the way. He dreamt of Sam, mostly, and how his brother was lost in a sea of ‘what if’ and ‘what am I?’ Dean wanted Sam to feel comfortable and loved; it made him sad to think that his brother was probably still unsure, that he probably felt broken. They were pulling down a long driveway on a property out in the middle of nowhere. Dean assumed it was the cabin; it wasn’t as fancy as Dean had expected, not that he was going to complain; camping was supposed to be about getting back to nature anyway, not the bullshit stuff the rich and elite did for fun.

 

“Ah, good, you’re awake.” Cain smiled and rubbed Dean’s hair playfully. “Help me get out of here so I can crash face first into a damn bed.”

 

“Right.” Dean climbed out and grabbed their bags to haul inside, while Cain got the door. It was a quaint and nice cabin, only a few rooms, nothing elaborate. It was _strange_ to see Cain being so casual; he was in jeans and a long sleeved shirt and not a suit first of all, not to mention he seemed more relaxed here.

 

“I like you like this,” Dean said as he helped Cain lay down. He was tired too, even after all of the sleeping he’d done.

 

“Like what?” Cain asked as Dean pulled off his boots.

 

“Casual. Relaxed. It’s nice.” Dean paused long enough to strip out of his jeans, blushing when he remembered he’d kept the panties on. “They really are comfortable, they feel nice on my johnson.”

 

Cain chuckled and patted the bed, so Dean quickly climbed in, snuggling up right next to Cain again. The man was surprisingly an excellent cuddler. It wasn’t long before Cain was asleep but Dean stayed awake, his head rest along Cain’s chest. The loneliness of missing his brother was filling his chest; he hadn’t seen Sam in a while. Maybe he would be able to go up for Thanksgiving this year.

 

The sound of crickets and something else - buzzing? - filled his ears. They were a good thing to be lulled to sleep by; reminded him of home and the country. He’d never been a city boy, that had always been Sam’s gig. Living in Chicago had been and still was a huge change for him. He’d gone to the University of Chicago because they’d given him the most money; he’d only applied at all because Sam had begged him. Something about the swim team, so he’d done it. But, part of him, still missed Kansas, and he’d considered transferring back to KSU, since it would save money, but he liked the programs at UC.

 

Even though he still had no idea what to major in.

 

He’d been Undecided his freshman year, and he was still technically Undecided this year too. There were too many options and now he was a kept boy; was that a lifetime gig? Could be Cain’s forever? _Don’t be stupid, of course not. Dude’s old. He’ll end up dying on your stupid ass and then what? You think he’s really gonna leave his fortune to_ you _? Yeah right._

 

Dean tightened his grip on Cain; thinking about death was not exactly what he’d had in mind. Existential thoughts tended to leave him waking up in a panic and calling his mother to make sure she and Sam were both okay. He still had homesickness, even though he’d gotten used to living in the city all year last year, and for most of the summer, since he’d had to return for swim team practice. _What would she think of you now, hm? In the arms of some guy who could be your father? Maybe your grandfather? She’d probably call the cops because what the fuck._

 

“One,” Dean whispered.

 

He shut his eyes as tightly as possible; until he saw the cosmos.

 

“Two.”

 

He took a deep breath before his panic started to set in.

 

“Three.”

 

There was nothing wrong with enjoying himself with Cain; the man was kind, and he just wanted company. Plus, the money. He’d already been paid one thousand dollars, which was a check he had yet to cash still.

 

“Four.”

 

Maybe Cain would take him to the bank after their trip was over. Maybe he’d splurge and buy himself a better laptop, since his was a piece of shit.

 

“Five.”

 

The anxiety was beginning to seep away.

 

“Six.”

 

Dean opened his eyes and then shut them again as he grew too tired to keep them awake. He never even made it to the count of seven.

 

* * *

 

The smell of cooking bacon roused him from sleep and Dean practically crawled to the kitchen to see what was being made. He groaned, leaning tiredly against the counter; his body was convinced he had jet lag.

 

“Tired?” Cain asked, even as he set a big mug of coffee in front of him, followed by a plate of eggs, bacon, toast, and hashbrowns.

 

“There is a God,” he mumbled as he sipped the coffee and pulled a face. “Ew, what the fuck is this shit?”

 

“Too strong?”

 

“Just inject the caffeine with an IV, I think that’d be less potent.” Dean reached for the cream and sugar Cain offered, dumping as much sugar in the beverage as possible in hopes of making it less bitter. “How can you drink that? Jesus.”

 

Cain shrugged. “Used to it, I suppose. You eat up, I’ll be out back.”

 

“You’re not going to eat?” Dean asked.

 

Cain smiled and pressed a kiss to the top of his head. “Not before the bees.”

 

He wasn’t even sure what to say to that, he just watched Cain walk out the back door. Was that some weird old dude saying he didn’t know about because he was still too young? Was he going to say that shit when he reached Cain’s age? Maybe he’d ask Cain how old he was before making _that_ assumption; just because the guy had gray hair didn’t make him Hugh Hefner.

 

Shoveling in his food absentmindedly, Dean watched as Cain reappeared in the weirdest hazmat suit Dean had ever seen. He blinked and stood, going to the back window to watch; the bastard hadn’t been kidding about _bees_. There were fucking bee boxes in the backyard, which Dean supposed was the source of the buzzing he’d heard last night. _Not before the bees._ Dean snorted and laughed, shaking his head as he went back to finish his breakfast.

 

Immediately, Dean thought of Castiel Novak, who would have peed himself from being so damn excited about the _bees_. The guy was completely mental about bees and saving the environment. Castiel had bee shirts, bee socks, bee hats, bee scarves, bee everything; Dean was fairly certain the guy probably wore bee underwear. Not that he’d ever peered down Castiel’s jeans to find out. Dean’s smile widened as he envisioned Castiel and Cain getting into a conversation about bees and how _great_ they were.

 

Half tempted to text Castiel about the bees, Dean had to stop himself, because then he’d have to explain what he was doing with Cain, et cetera. It would just be a giant mess. The bees would have to wait. Cain rejoined him a while later, back in his regular clothes. Dean stared at him with a smirk on his lips.

 

“What?” Cain asked.

 

“Bees, huh?”

 

“Yes, I keep bees,” came the defensive reply. “So?”

 

Dean shrugged. “Who watches ‘em when you’re gone?”

 

“I have friends who take care of them,” Cain replied.

 

“There’s this kid at school who’s like… point five steps away from turning into a bee.” Dean grinned, watching as Cain walked over to help himself to breakfast. “His name is Castiel Novak and-.”

 

“Novak?” Cain looked over at Dean and nodded slowly. “Yes, I know Castiel Novak.”

 

“You do?” Dean frowned. “How do you know him?” _Shit, was Cas one of his boys. Shit. Shit. That’s too weird._

 

“He had an internship with me,” Cain said, drawing Dean out of his naughty and awkward thoughts. “At my company. Secretary.”

 

“ _Oh_.” Dean visibly relaxed. “Thought you fucked him or something.”

 

“I do not have sex with my interns,” Cain said as he sat down slowly. “However, I did sleep with him promptly after his internship was over.”

 

Dean choked on his coffee. “You can’t be serious?”

 

Cain shrugged. “I am.”

 

“What the _fuck_ , man?” Dean shook his head and stood up. “Okay, here’s the deal. _You_ are going to tell me where your dick’s been for the past sixty years, and I’m going to try not to vomit.”

 

Cain frowned, looking honestly offended. “I am only thirty-five, Dean,” he said angrily. “I slept with Castiel Novak once. It was not a love affair. He came by, upset, I comforted him.”

 

“By putting your dick up his butt?” Dean scoffed. “Right, what a _great_ comfort tool. There, there Cas, let me just shove this up- _right there_. Yeah, see, we can _all_ feel better.” Dean glared, unsure why he felt so offended. Maybe because he didn’t want Cain to replace him, which he had done with every other boy he’d had.

 

Cain said nothing, which worried Dean. Maybe he’d gone too far? The silence continued, the only sounds being a ticking clock and the scrape of Cain’s fork and knife on the plate. Dean angrily stormed back to the bedroom to pout. Okay, so sometimes he didn’t act his age; so what? Eventually, Cain came to stand in the doorway, his eyes piercing and angry. Dean continued to glare at nothing.

 

“Why are you angry, Dean?” Cain asked.

 

“I don’t know.”

 

Cain walked over to sink onto the bed beside him. Dean refused to look at him, his arms folded over his chest,and his lips pursed. “You are angry because I slept with your friend.”

 

“Castiel isn't my friend. Just a guy I go to school with.”

 

“But you are angry I had sex with him.”

 

Dean looked over at Cain. “ _Yeah_. Who else have you fucked at my school? Am I just another notch in your belt? Is that it? I’m just another piece of ass to you?”

 

Cain’s eyebrows lifted as if he’d seen the light. “I see… You are _angry_ because you think I am going to find someone younger and more fun than you.”

 

Dean glared; he felt ridiculous glaring in pink panties, but he had no choice. “I didn’t _say_ that.”

 

“You didn’t have to.”

 

Dean angrily went to stand up but Cain grabbed his arm; not hard, in fact, Dean could have easily pulled away, but he didn’t. “What?” he asked, staring at the window.

 

“I am not going to throw you away like your father did,” Cain said quietly. “I am not going to replace you or toss you out like trash, Dean.”

 

Tears were stinging his eyes. Again. Dean glared and shuffled his feet, wanting to stay angry, but he couldn’t. “You promise?”

 

“I swear.”

 

Dean turned and climbed back onto the bed, lying against Cain’s side again. He realized that the money didn’t really matter to him. Not really. Cain could have taken the cash away and he would have stayed. At least, in the moment, he would have.

 

“Are you alright now?” Cain asked, petting Dean’s hair. Dean wanted to purr, it felt so good to be loved and petted on.

 

“Yes,” he said quietly. “We’re good.”

 

 


	5. Chapter 5

A month had passed since he’d first moved into Cain’s and he hadn’t received a call from his mother asking about the money. He’d made another one grand before Cain had gone to work, and he’d finally had the time to go and put the cash in his bank account. Since he had the day off, Dean decided to walk to the closest Apple store and pick out a laptop. His was a piece of shit Windows computer and he was sick of it; Cain had let him use the desktop iMac at the apartment for homework and internet surfing, but he wanted his own laptop.

 

In the past month Cain had bought him many things, which had appeared subtly. New clothes; new jeans, new shirts, new shoes, new underwear (more panties), and even a new leather jacket. Cain had bought him a PS4, which was definitely the reason his grades were slipping, but he couldn’t help it; _The Last of Us_ on the new console was _amazing_. So was _Far Cry 4_ and the new _Assassin’s Creed_. Dean spent more time at the apartment than he did school, which was also probably why his grades were slipping, which wasn’t good for the swim team. He just hoped Cain didn’t find out, or he had a feeling he’d _actually_ be in the trouble.

 

Dean walked to the Apple store with two grand in cash, happy to lay it down for a new laptop, even if he had told himself to put one grand toward his tuition. That would be next month, or maybe that would be the bonus Cain had promised him in a few weeks. Laptop in hand, Dean walked back to campus to pick up his car; Cain had given him a parking pass so he could finally put his car in the parking garage beneath the building. He was four feet away from his Baby when he heard his coach call his name. Dean spun around.

 

“Haven’t seen you around much, Winchester,” Henriksen said as he walked up to him, looking disappointed. “You quittin’ the team?”

 

“No,” Dean said quickly. “Sorry, I know I’ve been behind… Family stuff.”

 

“Hm. Well, get your ass in the pool today and I’ll consider keeping you around.”

 

“Yes, Sir. Can I drop this off first? I don’t want to leave it in my car.” Dean held up the Apple bag and Henriksen nodded.

 

“Fifteen minutes.”

 

“Yes, Sir.” Dean jumped into the car and took off back to the apartment building. He couldn’t afford to lose his athletic scholarship; it covered half his tuition. Dean left the keys with the valet guy, even if it made him nervous, and then he was dropping off the laptop, and then back outside to rush over to the pool. Dean barely made it into the water under fifteen minutes, but he was doing laps right at the fifteen mark, pushing himself harder than necessary.

 

“Slow down!” Henriksen yelled at him. “Don’t need you pulling something.”

 

Dean paused to take a breath. “Sorry,” he said before returning to making laps at his usual pace.

 

“Surprised you’re doing so well, where you been swimming to keep up?” Henriksen asked as Dean did his seventh lap.

 

He paused at the end, removing his goggles to look up at his coach. “New place I’m staying,” he replied with a shrug.

 

“Hm. Well, I suppose you can stay on the team, but next meet, you better break that record, Winchester. I’m counting on you.” Henriken walked off to yell at a few freshman dicking around and Dean relaxed. The meet was this weekend, he’d finally had a chance to check his calendar. It was away; he had to travel to Kansas, which was ironic, since he’d been avoiding his mother for a month. She’d probably bring Sam along and insist they have dinner that night. He hoped Cain didn’t mind him going away for the weekend.

 

He took a deep breath and hauled his body out of the pool. Only one way to find out. Dean walked off to the lockers and showers, removing his phone from his locker to give Cain a call. Not that he would answer or at least Dean hoped; he could leave an embarrassed message, which would be easier than directly confronting the guy.

 

However, Cain _did_ answer, and Dean’s heart sank. “Good afternoon, Dean.”

 

“You’re not at work?” Dean asked, his voice squeakier than he’d intended.

 

“I got off early… But you aren’t here.”

 

“Sorry, I’m at the pool. Ran into my coach, said he wanted me in the pool ASAP. Almost got in trouble.” Dean blushed and ran his hand along the back of his neck. “Um, look, I called because I sorta have this meet this weekend, away at Kansas, and I won’t be here this weekend. I wanted to let you know.”

 

“Kansas?” Cain asked, sounding curious, not angry. “Sounds… fun.”

 

“Oh, it’ll be okay.” Dean shrugged. “It’s no biggie.”

 

“Would you like an escort?”

 

“No!” Dean called, a little too loudly. “I mean- it’s just, it’s a team thing, and I have to go on the bus with them and stuff. It’s really no big deal, you don’t gotta take the whole weekend off to spend time with me. Really.”

 

Cain didn’t say anything for a moment. Dean almost asked him if he was still there, but finally he spoke, “I see. Well, I cannot keep you from your athletic events. What time are you leaving?”

 

“We’ll Friday morning. Probably six-ish.”

 

“And when will you return?”

 

“Sunday night. Not sure when, but we’re usually back before midnight.” Dean glanced around the room, glad he was alone. “So, this is cool?”

 

“Yes… it’s… _cool_.”

 

Dean grinned at Cain using his language; it was amusing. “Awesome, see later.” He hung up and returned his phone back to his jean’s pockets. Practice. He really needed to practice.

 

* * *

 

 

“ _Honey_!” Mary squealed and wrapped her arms around him when she opened the door. Dean smiled and hugged her back; he hadn’t called, he had just wanted to be a surprise.

 

“Hey, Mom,” he said, kissing her cheek.

 

“What are you _doing_ here?” she asked, stepping aside so he could come in. Henriksen had let him off the hook so he could go and visit with his mother and brother, which had been ridiculously nice of him, since Dean hadn’t been the perfect teammate lately.

 

“I’ve got a meet this weekend. I can’t stay too long, but um, Coach let me drop by for a few hours.” Dean smiled and followed her back to the kitchen, which was where Mary spent most of her time anyway. “Where’s Sammy?”

 

“Oh-.” Mary turned to face him, lowering her voice. “Sam wishes to be called Samantha, that is… her choice, Alright?”

 

Dean blinked. When had Sam decided to be _her_ and not _him_? “Whoa, what?” Dean stammered, but then Sam was rushing around the corner to hug him. “Hey!! Sammy!”

 

Sam squeezed him back, pulling away when they’d hugged for what felt like forever. “Dean. What are you doing here?”

 

Dean looked Sam over, his eyes trailing up the long, shaved legs, to the skirt Sam wore - pink, plaid - up to the white shirt, fitting his (her?) body snugly, and up to the long, dark hair which Sam wore in a high ponytail. Sam’s eyes were decorated in makeup. It was odd, to see Sam so… different.

 

“Wow, look at you,” he said with a quick smile. “So, um, Samantha, huh?”

 

“Yes,” Sam said. “But you can still call me Sammy and Sam, Dean. They’re gender neutral enough, it doesn’t bug me too much.”  

 

“Cool…. Um…” Dean rubbed his neck, unsure of what else to say. “Look, if I fuck up, I’m sorry, it’s just an adjustment-.”

 

“I know,” Sam said with a kind smile. “If you call me him, it’s okay. I know it’ll take a while to adjust. Mom’s still adjusting too. It’s okay, I won’t get mad… I mean, if you do it on purpose, that’s different, but accidental is understandable.”

 

Dean glanced over at his mother tentatively before nodding and giving Sam a smile. “Yep. No problem.”

 

“So, what are you doing here?” Sam latched onto his arm, pulling him back to the living room to sit on the couch.

 

“Got a meet this weekend. Wanna come? Look at the cute boys?” Dean teased, tugging at Sam’s ponytail gently.

 

“Shut up,” Sam (no, Samantha, damn it) giggled. “Mom would _kill_ me.”

 

“Yeah, you’re only fifteen, but hey, whatever.” Dean shrugged and leaned back against the couch.

 

Samantha (there, he could see Sam as Samantha) smiled and leaned against him. “I missed you, Dean.”

 

“I miss you too, Sammy. All the time. So, you wanna come back with me to the meet? I got a hotel room, you can hang out. I’ll have to sneak you in, but whatever.”

 

Samantha blushed and nodded, pressing into Dean. “Okay. How are we gonna sneak me in?”

 

Dean grinned. “Don’t worry, I got this.”

 

* * *

Sneaking his little brother (no sister, _sister_ ), was harder than Dean had first imagined, but he eventually got Samantha into his room with him and then they burst into giggle fits over how ridiculous it all was. After, Dean watched Samantha walk around (maybe he’d just think of Sam as Sammy until he adjusted), wanting to dive into so many different questions, but he held back. It would probably be rude to prod and pry.

 

“You want to ask me why, don’t you?” Sammy asked (yes, easier on Dean to see Sam as Sammy for now).

 

He shrugged. “Yeah. But I don’t wanna upset you.”

 

“It started with me not really knowing what I wanted,” Sammy replied as she sat down on the bed with him. “I didn’t feel right as a boy, but I also wasn’t sure I wanted to be a girl either… until I tried on some of Mom’s makeup and then I knew.” She blushed and let her hair down, pulling at it nervously. “I tried on lipstick and I just knew.”

 

Dean nodded, reaching over to tilt Sammy’s chin up. “Hey, it’s okay. I’m adjusting, I swear.”

 

Sammy smiled and hugged him again. “Thanks, Dean… I couldn’t have done this while Dad was around, but… I feel better about myself now.”

 

“You wanna get the surgery and stuff?” Dean asked, letting Sammy cuddle him.

 

“Yeah. I’m too young, or that’s what the doctor’s said, but Mom is getting me estrogen so I can start to transition. It’s a long process; I spent all year last year in therapy to “make sure” this is what I wanted.” Sammy rolled her eyes.

 

“How the kids treating you at school?” That was the one thing Dean feared the most; he didn’t want Sammy to end up as another statistic because the kids were overly cruel to her. “They mean?”

 

“Mom had me transfer to a new school as Samantha Winchester. No one knows I’m… actually a boy, so…” Sammy shrugged. “It’s better. They even have gender neutral bathrooms at the new school, it’s nice.”

 

“Hey, that’s cool.” Dean smiled and started to pet Sammy’s hair; it was long and silky. Dean had to admit, he was a little jealous of Sammy’s hair. “I’m glad you live in a place you can be who you want to be, Sammy. It’s nice to know you won’t get your ass kicked by Dad or the kids at school.”

 

“Yeah,” Sammy whispered, burrowing into Dean’s side. “You sure it doesn’t bug you? Having a little sister?”

 

“ _Nah_ ,” Dean said with a wave of his hand. “It’s whatever. I still gotta protect your ass from everything anyway, so what’s the difference?” He teased Sammy’s side, making her giggle and laugh. “Actually, I know you can take care of yourself. You’ve always been able to do that.”

 

“Thanks.” Sammy smiled and relaxed. “So, cute boys on the swim team, huh?”

 

Dean smirked. “Yeah, but if they touch you I’m gonna cut their balls off, got it?”

 

“Jerk.”

 

“Bitch-.” Dean broke off. “Is that still okay?”

 

“ _Yes_ , Dean. I know it’s our thing.” Sammy smiled and kissed his cheek, leaving behind a trace of lipgloss. “So, how’s your love life been treating you?”

 

Dean blushed and thought on Cain; he hadn’t been very snuggly the night prior to Dean’s leaving and he hadn’t said anything to him before he’d left. It had been a strange shift from the days previous. “Um, pretty empty right now,” he said slowly with a shrug; he wasn’t ready to tell anyone yet. Maybe he’d never be ready.

 

“Seriously? Stud like you? I don’t believe it.” Sammy sat up on her knees, pulling her long hair back again. “C’mon Dean, spill.”

 

Dean sat up too, taking a deep breath. “If I tell you, you have to _swear_ on Bones’ grave that you won’t tell.” Sammy gasped and covered her mouth, knowing it was _serious_ when Dean brought up their childhood dog. “Swear?”

 

Sammy nodded. “Swear.”

 

“I’m… seeing an older man,” he said slowly. “Sorta… He’s… paying me to live in his penthouse with him and, um, I masturbate for him? We haven’t had sex yet, but he’s given me a handy or three… Spanks me…” Dean blushed and dropped his eyes back to the bedspread. “Calls me his sub, I don’t realy know what that means but-.”

 

“Oh my _God_ ,” Sammy gasped. “Dean, you’ve got a sugar daddy!”

 

“A- a what?” Dean stammered. How did Sammy know these things and he didn’t?

 

“A sugar daddy. An older, rich guy who buys their younger partner gifts and things in exchange for sex. _Wow_. Look at you, getting a good deal.” Sammy blushed and smiled. “I wanna be a sugar baby, that’d be awesome.”

 

“You are _too_ young to be doing what I’m doing,” Dean said firmly. “Got it?”

 

“Yeah, _yeah_.”

 

“Anyway, calls me his sub and stuff… I haven’t looked it all up yet, I’m a little afraid to Google, but it’s been a nice set up. Been able to pay for a sweet new laptop, dude. It’s an Apple.” Dean grinned and jumped up to remove it from his bookbag to show Sammy.

 

“No way. That’s cool.” Sammy watched as Dean brought the laptop back. “Is the guy hot?”

 

“Yeah, he’s a silver fox… I like him. He’s real nice to me… Except before I left, I think I upset him or something. I don’t know.” Dean shrugged and opened up the laptop to show her. “Neat, yeah?”

 

“Oh, _fancy_.” Sammy took it from him.

 

“Hey!”

 

“Gonna put stuff on it for you,” Sammy said dismissively.

 

“Oh right, forgot you’re a computer whiz. Thanks.” Dean settled in to watch her put apps and programs on the new laptop, happy to share some quiet time with Sammy before the meet in the morning.

 

 

“The guy you’re up against is the best swimmer in the State,” Henriksen said to Dean as they prepared for the freestyle stroke. “You beat him and you’ll break a whole new record.”

 

“No pressure,” Dean said lightly as he took a deep breath.

 

“Dean, the fact that you made it to the final round is damn good enough for me.” Henriksen smiled and squeezed his shoulder. “Kick some ass out there.”

 

He nodded and stood, walking over to his starting point. Dean knew his competitor was good at the backstroke, but Dean could only hope he was better at the breaststroke. The whistle sounded and Dean took off, prepared to beat the son of a bitch. It didn’t help knowing his team was counting on him, and his sister (see? he could do it) and mother were watching in the audience; cheering him on, wanting him to win.

 

_You can do this. Pretend there’s cherry pie waiting for you at the finish. Yummy, scrumptious, delicious, cherry pie_.

 

That was enough of a motivator to allow Dean to speed up, soon breaking free of his opponent’s stride. Dean touched the wall first, but now he had to turn around and do it again. The other guy was hot on his ass and Dean could feel his body tiring; he’d pushed himself too damn hard this meet. He had wanted to impress his coach and teammates, but now his body was exhausted.

 

_Come on. You can do it. Stop being a pussy_.

 

Dean’s opponent was beating him, that was much was clear, but Dean pushed himself harder, feeling his lungs scream for him to stop. He felt nauseous but he kept going, swimming harder, pushing himself past the breaking point. The wall was so close, he just needed to reach out and touch it. Dean used the last of his energy to burst through and slam his hand against the edge of the pool. After, the world exploded and Dean had to take a moment to stop himself from vomiting.

 

“We have a new winner! Dean Winchester of University of Chicago.”

 

Dean could hear the announcer, but he was too tired to get out of the water; he rested against the pool and pressed his forehead to the ledge. Henriksen knelt beside him, talking low. “Dean? You alright?”

 

“No,” he managed to say. “Feel like I’m gonna pass out or throw up.”

 

“Come on, get you out of the water, sit down, relax a little.” Henriksen helped him up, but Dean almost fell down as soon as he was free of the pool, which made the crowd slowly siphon off its noise. He glanced up at his mother, trying to give her a weak smile, but he could see her worry, and Sammy’s too. Dean allowed Henriksen to walk him out of the room entirely and back to the lockers so he could relax. As soon as he was away from everyone, he vomited all over the floor.

 

“I’m sorry,” he mumbled, trying to wipe his mouth, but Henriksen rubbed his back. “Pushed too hard-.”

 

“Easy, Dean.”

 

Dean didn’t make it to the lockers; he sank onto the floor, allowing his head to rest back against the wall in exhaustion. Henriksen left him to return with a bottle of water and some pills. “What are those?”

 

“Help your nausea. Come on, drink slow.”

 

Dean took the pills and drank the water slowly. His mother burst through the doors soon after, which he had to try and not groan about; he didn’t need her fretting over him while he felt like shit warmed over. “Ma, I’m okay.”

 

“You are not,” she said, kneeling beside him. “Are you sick?”

 

“I just pushed too hard, that’s all.” Dean pushed her hands away. “Ma, I need air, c’mon, cut it out.” He didn’t mean to hurt her feelings, but he wanted to relax on his own.

 

Mary glared up at Henriksen. “You should know better than to let him push himself so hard.”

 

“I’m sorry, Ma’am.”

 

“Mom, leave him alone. _I_ pushed myself. I wanted to win… and I did. I broke a record.” He smiled, the nausea finally subsiding. “I feel a little better, okay? I promise. I just need something to eat, I think. Where’s Sammy?”

 

“I had him wait inside,” Mary replied shortly.

 

“ _Her_ , Mom. Her.” Dean glared at his mother before allowing Henriksen to stand him up. “At least I didn’t faint in the pool.”

 

Henriken clapped his back and squeezed his shoulder. “Proud of you, Dean.”

 

“Thanks, Coach.”

 

“Now, what do you say to a little celebration?”

 

* * *

 

 

Dean stumbled back to his room tiredly; he’d gotten a little too drunk at the party, and now all he wanted to do was call Cain and have drunken phone sex. He giggled and let himself into his room. The sight on the bed made him do a doubletake; Sammy was being fucked by some guy. Dean snarled and walked over to yank the guy off of her, punching him in the face.

 

“Dean!” Sammy gasped, sitting up in alarm.

 

“Get your fuckin’ dick outta my sister, ya faggot,” Dean slurred.

 

“Dude, you’re _drunk_ ,” the guy protested, backing up.

 

“Dude, she’s fifteen. Beat it.” Dean watched the guy look at Sammy in alarm, gather up his clothes, and take off. Slowly, Dean turned to face Sammy. “What the _fuck_ is wrong with you, huh?”

 

Sammy looked away, covering up. “Shut up.”

 

“Dude, you are _fifteen_. Sex should be the _last_ thing on your mind, right now!” Suddenly, Dean felt extremely sober. “And why aren’t you at home? Where’s Mom?”

 

“She told me I could stay here with you since you had to go home tomorrow night anyway. Don’t you have another meet tomorrow?”

 

“Henriksen is letting me sit it out,” Dean replied with a shrug. “Get dressed and call Mom, you’re going home.”

 

“But Dean-.”

 

“I _said_ get dressed and call Mom.” Dean sank onto the bed. “Not gonna let you use the fucking hotel room for sex. Jesus H. Christ.”

 

Sammy blushed and redressed, doing as she was told. “I hate you.”

 

“No, you don’t.” Dean sank down onto the mattress. “Wake me up when Mom gets here.”

 

“Whatever. Fuck you, Dean. Fucking drunk.”

 

Dean frowned, surprised at Sammy’s vehemence, but he shut his eyes to sleep anyway.

 

Dean did not wake again until Henriksen pounded on his door to rouse him. Dean groaned, feeling sick and hungover; okay maybe he’d had _way_ too much to drink the night before. He was just thankful he wouldn’t be swimming today. He wasn’t even sure he wanted to go and watch the meet; every movement made his head hurt. By sheer luck, Dean made it to the door and pried it open.

 

“Jesus, you look like shit,” Henriksen said. “How much did you drink last night?”

 

Dean moaned. “Too much.”

 

“I want your ass at the pool, Dean. I don’t give a damn _how_ hungover you are.” Henriksen gave him a firm look. “Fifteen minutes, Dean.”

 

Dean waved him off and shut the door, slowly returning to the bed to do a faceplant. He didn’t make it in fifteen minutes; he didn’t make it at all. Not until he was being rolled over and Henriksen was glaring down at him. “Shit- what time is it?” he gasped, suddenly very awake.

 

“You missed the meet,” Henriksen said, his voice cold. “You may have broken a record, Dean, but your behavior is enough for me to suspend you.”

 

“What- Coach, _no_. I’ll lose my scholarship!” He stared up at his coach in panic; he couldn’t lose all of that money. He just couldn’t. “Please, don’t suspend me. I’ll be better. I’ll come to practice. I’ll go to the meets. I won’t get smashed again, I swear to God.”

 

“You are one of my best swimmers, Dean,” Henriksen said slowly, “but that doesn’t excuse you. You are suspended from the team for the next three meets. If you can prove yourself by coming to practice, doing as you’re _told_ , I will reconsider. Not before.”

 

He nodded, looking away. “Yes, Sir.”

 

“Good. Get your ass ready to leave.” Dean nodded and Henriksen left.

 

* * *

 

The apartment was quiet when Dean returned, feeling drained and in need for a long break, but he had class tomorrow. He sighed, walking over to the stairs, leaving his bag by the stairs, too tired to carry it up to his bedroom. It was almost midnight, so Dean walked over to Cain’s door, and knocked timidly; it opened after the second knock. He smiled and practically fell against Cain’s chest.

 

“Hi,” he said, his voice muffled.

 

Cain wrapped his arms around him but then he was pushing him back firmly. “Go to bed, Dean.”

 

He frowned. Cain was _still_ mad at him? What the fuck he had he done? “Dude, what did I do to upset you?”

 

Cain shook his head. “If you have to ask-.”

 

“Look, I am so not in the mood for riddles, I’m fucking tired, my brother is a girl, and Coach is pissed at me. So, _please_ , just tell me what I did so I can grovel.” Dean looked up at Cain in desperation; he couldn’t take more disappointment tonight. “Please.”

 

“You did not want me to go with you,” Cain replied stiffly.

 

“What?”

 

“When you told me about your meet, I figured you would ask me to come with you. But you were adamant on me staying home.” Cain shrugged and Dean could tell the man was wounded, even though he tried to cover it up. “But, I can understand… I am not exactly the _hippest_ person in the world.”

 

Dean softened and wrapped his arms around Cain again, forcing him to cuddle standing upright. “I didn’t ask you to come because I’m not exactly sure how to explain it to my Mom, that’s _all_.”

 

Cain huffed, but he returned the hug, and rubbed his back. “I watched it on the television. You were very good.”

 

Dean smiled and blushed, looking up timidly. “Yeah?”

 

“I am very proud of you winning, Dean.”

 

“Aw, shucks, thanks old man.” He winked and kissed Cain’s chin playfully. “I missed you while I was away from you, ya know.”

 

“Is that so?”

 

“Almost called you for drunk phone sex, but my sister-brother was fucking some dude, so-.”

 

“You’re _what_?”

 

“Oh, Sammy’s a girl… Sorry- sister-brother was really rude- Fuck I didn’t mean it like that. I’m tired- I’m sorry. Don’t tell him- _her_! Her.” Dean blushed and continued to stammer stupidly. “Sam was a boy but now she is a girl.”

 

“I see.”

 

“She makes a pretty girl, but I caught her fucking a guy, and I punched the dude’s lights out, and now we’re kinda fighting… I just hope she doesn’t stay mad forever.” Dean allowed Cain to walk him into the bedroom and place him on the bed. He sighed happily when Cain kissed him and began to pull his clothes off; it wasn’t long before he was naked, his legs spread, and Cain was resting on top of him; he could feel Cain’s bulge pressing right against his ass.

 

“I missed you as well, Dean,” Cain told him, his voice dark with want and lust. “Are you too tired for this?”

 

Dean smiled sleepily and kissed Cain’s lips over and over, not wanting to stop. But he could feel sleep yanking on him. “Yeah, sor-sorry.”

 

Cain nodded in understanding and then he eased off of Dean and pulled him under the blankets. Dean sighed and it wasn’t long before he was out like a light.

 

 


	6. Chapter 6

**Notes for the Chapter:**

> Please do not have sex with your partner while he/she is asleep without their prior consent.

Dean woke up in orgasm.

 

He cried out and let his eyes fly open as he sat up to stare down at Cain who was licking his hole and fingering it. “Shit,” he gasped, his eyes wide. “Jesus, what a way to wake up.” Dean fell back onto the mattress and stared up at the ceiling. “God _damn_.”

 

Cain released his hips and sat up and Dean jumped at the sound of a package being opened. He shifted to see Cain putting on a condom and Dean felt his body ache; Cain’s cock was _big_. Bigger than he’d first imagined. He shivered and smiled a little, the smile turning to a slight grimace as Cain began to push in. The orgasm made it easier, but he still flinched now and again, clenching onto Cain tightly.

 

Cain kissed him then and Dean kissed back, eager for the affection. He didn’t care if it was early or if the sun wasn’t even up yet. He just wanted to be fucked sleepily into the bed. Cain rested inside of him, pressing kissing to his lips and neck, letting Dean relax, and grow used to the feeling of being stretched open.

 

“You didn’t have to put on a condom,” Dean muttered sleepily.

 

Cain slid his hands to Dean’s wrists, slowly pinning them over Dean’s head; it was a gentle motion, but Dean enjoyed being held down by Cain’s body. It felt good, to be feel so powerless. “It is common courtesy,” Cain replied with another kiss. “Now that I know you do not mind, I will not wear one the next time.”

 

Dean sighed and nodded, wrapping his thighs around Cain’s hips. He groaned and tilted his neck up for the offering. “Fuck me,” he growled. “Please.” Cain pulled his hips back and then pressed in just as slow as the first time, making Dean whimper. “I said _fuck_ me.”

 

“Patience,” Cain whispered against his neck, as he started to suck bruises into Dean’s skin. The older man began to speed up, slowly pistoning his hips into Dean, but as Dean loosened up, the faster and harder Cain fucked.

 

“Yes, _yes_ ,” Dean panted and growled, wriggling around until Cain forcibly held him down. He whined and keened at the feeling; losing control felt indescribably good. He was going to come again and soon, but he wanted to hold on. The bed started to thump against its headboard and Dean grinned as Cain fucked him harder.

 

“Figured,” Cain growled, slamming him hard, “you deserved, a _reward_.”

 

“F-for _what_?” Dean panted, arching his chest into Cain’s eagerly.

 

“Winning.”

 

Dean smiled and sighed, finally coming his load against Cain’s stomach. Cain grunted and kept fucking him; Dean remained still and limp, giving himself up completely. Right before he could grow too stimulated, Cain finished with a long groan and a rough bite against Dean’s chest. Cain pulled off of him and was quick to dispose of the condom, but Dean whined, reaching for his lover needily. He wanted to cuddle.

 

“Just a moment,” Cain chuckled as he eased back down onto the mattress to spoon Dean. “I _do_ enjoy your eagerness.”

 

Dean blushed and pulled Cain’s arm over his body. “That was good,” he whispered. “I liked it.”

 

“Good. I think it’s time we talk about safewords.”

 

“What the fuck is that?” he asked, twisting to look Cain in the eye.

 

“It is used in lifestyles such as ours,” Cain replied slowly. “A safeword is used when someone has had enough and they wish to stop.”

 

“Isn’t that what _no_ is for?” Dean asked, rolling onto his back so he didn’t have to twist awkwardly.

 

“Yes, of course, but a safeword is not a word associated with sex. They are very important,” Cain said, his tone very serious. Dean huffed and shrugged. “Dean, I’m serious.”

 

“I know, I’m just not sure what to use.” He turned his eyes up to the ceiling as he tried to think. “Any word?”

 

“Any word,” Cain confirmed.

 

“Impala.”

 

“Impala?”

 

“Yep.”

 

Cain kissed him. “Good. Very good.”

 

Dean smiled and kissed his lover back, feeling his cheeks heat up. Cain always made him blush, every time he was praised. The guy knew how to rile him up. “So, what _is_ a sub and dom anyway?”

 

“A dom or dominant, myself, is a sexual and life partner who take the superior control in the relationship. A sub or submissive, _you_ , take less control. Does this make sense?” Cain asked, his fingers running up and down Dean’s smooth stomach.

 

“Yeah,” Dean said with a nod. “So, because you top me, I’m a sub?”

 

“Not necessarily. You are sub because you are eager to please me and you allow me to make the rules. You accept punishment.” Cain started to kiss along Dean’s neck again, trailing down to his chest, and pressing his lips over Dean’s nipple. Dean groaned, feeling his toes curl.

 

“Oh _hhh_.”

 

“Do you understand?” Cain asked quietly.

 

“Y-yeah,” he panted, feeling his cock stir again. “Shit-.”

 

“Touch yourself,” Cain muttered. Dean could hear the command in his voice; soft, but stern.

 

“Yes, Sir,” he whispered as he trailed his hand down to stroke his cock, using his cum to slick the tug and pull. “Is this- _good_?”

 

“Yes,” Cain told him. “I have a proposition for you, Dean.”

 

“W-what?” Dean panted, trying to focus on _not_ coming.

 

“This weekend, there is a… party happening. I wish to take you.” Cain trailed his fingers through Dean’s hair, kissing his lips playfully. Dean whimpered and kissed him back, pressing into his own hand.

 

“What kind of party?”

 

“Not the kind you are used to.”

 

Dean licked his lips and sped up his hand. “Y-yeah? W-what- what- _oh God_ \- what happens? At these… parties?” Dean shut his eyes, trying to hold back; it had been a month, and he still felt as if he was a quickshot. It was embarrassing and annoying.

 

“I have some friends who are like me and some who are like you,” Cain replied tentatively. “You can imagine what goes on.”

 

Dean gasped and came, coating his stomach and chest with his thick load. No matter how many times he jerked off, his spunk stayed thick, like he hadn’t in days. “Shit- _shit_ , I’m sorry.”

 

Cain chuckled and kissed his temple. “Do not apologize for getting off.”

 

“I know I’m too quick-.”

 

“You are doing well,” Cain corrected him, “which is why I wish to take you to this party.”

 

Dean looked up sheepishly. “It’s a sexy party, isn’t it?” Cain nodded and Dean felt a blush heat up his entire body. “Do other people have to fuck me? Or just you?”

 

“That is up to your own discretion,” Cain replied. “I would never put you in harms way, Dean. You can trust me.”

 

Dean gulped and pressed his face into Cain’s chest. “I don’t know,” he mumbled. “Seems too fast and too soon.”

 

“I understand.”

 

“Maybe, start smaller?”

 

“How so?” Cain asked.

 

“I dunno… Invite a friend of yours over?” Dean gulped and stared down at the bed. “Just one, though.”

 

“I can do that.”

 

“‘Kay,” he whispered, snuggling back in.

 

“Do you wish to fuck again?” Cain asked him quietly.

 

Dean whined and nodded. “Please.” He gasped and laughed when Cain flipped them back over.

 

* * *

 

The guy who came over to Cain’s apartment was not what Dean had expected. He wasn’t wearing a suit, nor did he look all that fancy or high bred; he had a trimmed beard and sparkling blue eyes surrounded by deep laugh lines. When the guy spoke, his accent made Dean’s body tingle.

 

“Evenin’,” the guy said to Cain with a warm hug. “Good to see you, brother.”

 

Dean sputtered. “You’re not-.”

 

“Not related,” Cain confirmed. “Dean, this is Benjamin Lafitte.”

 

“Pah, call me Benny.” Benny held out hs hand and Dean shook it weakly; seriously, Benny’s accent was making his panties wet. “He’s cute, Cain. Nice lips.”

 

“He’s quite good at using his lips,” Cain said with a devious smirk, which made Dean blush even deeper. “Dean, will you remove your clothes?”

 

Damn, they weren’t about beating around the bush. Dean gave a nod and walked away to strip in privacy; he didn’t mind taking it all off in front of Cain, but for some reason, doing it while both Benny and Cain watched him, made him feel more self conscious. The men continued to talk quietly, but Dean was too far away to make out what was being said, so he just focused on taking everything off, except the panties; he had chosen a little black number that laced up in the back like a corset. Cain had picked them out especially for tonight.

 

Taking a deep breath, Dean walked out, trying to carry himself confidently. Benny and Cain turned to look at him, both of their gazes hungry, stripping the panties away with their eyes. “Is this satisfactory?” he dared to ask, gesturing at himself.

 

“Oh, _yeah_ ,” Benny purred with a hungry shark’s grin. “Gorgeous, Cain, one of the best I’ve seen in your home.”

 

Dean continued to blush, staring down at his toes as he dug them into the plush carpet; the fibers tickled the arches of his feet, sending goosebumps up his legs and along his thighs. He’d shaved the night before, making sure all traces of hair was gone from his body, since it was always growing back, no matter how much it shaved. It was annoying being a swimmer and Dean had an immense respect for women due to his shaving habits.

 

“May I?” Benny asked, looking to Cain for permission. Dean glanced up, unsure of what that meant.

 

“May he touch you, Dean?” Cain asked, clarifying the situation.

 

“Oh, yeah, yeah, sure.” He nodded and stood still. Benny walked up to him and cupped his cheek, and Dean found himself pressing into Benny’s touch, while the man’s other hand slid down from his shoulder to his chest, tweaking Dean’s nipple with just his thumb. Dean groaned and he had to reach out and grasp onto Benny’s clothes to steady himself.

 

“Gorgeous,” Benny praised, kissing Dean’s neck and cheek. Dean turned to get a kiss on the lips, blushing shyly, which made Benny chuckle.

 

“May I suck your cock?” Dean asked. Benny laughed and nodded, to which Dean sank to his knees and pulled open Benny’s belt and fly. Before Benny had come over, Cain had told him that it was perfectly fine for him to have sex with his friend, or not, that was completely up to Dean. Benny’s cock came free into Dean’s hands and he licked his lips at the site of the thick member; he was longer than Cain, but just as thick. He slid Benny into his mouth with the slutty eagerness he was becoming known for.

 

“Ah, _fuck_ ,” Benny cursed with a deep groan. “He’s fucking _good_.”

 

“Yes, he is,” Cain agreed as he walked over to run his fingers through Dean’s hair. “Such a good boy.”

 

Dean shut his eyes and relished in the praise and Benny’s musk; it was too much. His cock was hard in the panties, straining, and staining the fabric, but he didn’t touch himself, since he hadn’t been given permission. Instead, Dean continued to suck Benny slowly and gently, unsure of how much pressure to use.

 

“You ain’t gonna break me, Sugar,” Benny told him, seeming to understand Dean’s hesitation. “Just watch the teeth is all.”

 

He looked up at Benny, knowing Cain liked it when he looked up, his mouth full of cock. His eyes sparkled and he sucked harder, bobbing his head with more intention. Dean wanted Benny to finish in his mouth; he wanted to open his lips and show it off before he swallowed. Again, Dean shut his eyes and worked, wondering when he had turned into such a slut.

 

“He’s good at takin’ orders, ain’t he?” Benny asked with a devilish grin.

 

“Oh, yes,” Cain agreed, still petting Dean’s hair now and again. “Very good.”

 

“Good to know- _oh_ fuck,” Benny grunted, forcibly holding back from fucking Dean’s face. “Glad you invited me over to play with him.”

 

“He is too, I can assure you,” Cain said with a fond smile.

 

Dean whined in response, speeding up, trying to get Benny off now. He ran and wrapped his tongue along Benny’s length, running it along the slit leaking salty precome. Listening to Benny’s grunts and sighs, Dean sped up or slowed down, making sure to drag out the pleasure just a little longer. His own whimpers and moans ran down Benny’s length in little vibrations.

 

“Such a good boy, Dean,” Cain praised, which was enough for Dean to start coming in his panties, making a sticky mess. He whimpered pathetically and then Benny was coming in his mouth, which he jerked, not expecting it; he pulled back, ending up with a facefull of cum.

 

“Oh, _Jesus_ ,” Benny hissed at the sight of Dean covered in his load. “Sorry, Sugar. Shoulda warned you.”

 

Dean sighed and shut his eyes, licking his lips and catching the bit dribbling down his chin. “Thank you,” he said sincerely. _Fuck,_ had that come from?

 

“So polite,” Benny said with a wink. “I like polite boys.”

 

Cain helped Dean upright, peering down his panties. “You wet your panties,” he said, looking up at him with a smirk. “Did I give you permission to come? Did Benny?”

 

“No,” he squeaked, his toes wriggling in the carpet nervously. “I’m sorry.”

 

“Take these off, you’ve ruined them.” Cain tsked and Dean did as he was told, tossing the panties to the floor. “Now, bend over the couch.”

 

Dean nodded, a little bit of adrenaline rushing through his system as he walked over to bend over the couch like a good boy. Dean bent so far over, his head was more or less in the cushions, his toes pressing into the floor dangerously so he didn’t tip himself over, ass over head. He felt one of them stand behind him and then there was the warning _woosh_ in the air before his ass was spanked hard. Dean cried out, gripping the couch to keep still, realizing quickly that Benny and Cain were taking turns to spank him; one would go and then the other.

 

It wasn’t long before his ass was red and sore, but he wanted more. He hadn’t called out his safeword, so the punishment continued. Dean breathed heavily, sweat making his flesh sticky, and his cock dripping more precome on the couch and along his thighs. He was going to come _again_ and he still hadn’t been given permission. He squeezed his eyes shut and tried to focus on something else, anything else.

 

“I see you are close to coming,” Cain said quietly. The spanking stopped for the moment, which Dean was grateful for. “Did either of us _tell_ you that you could come?”

 

“N-no, Sir,” Dean panted, trying to relax and recover from edging for so long.

 

“You are not allowed to come,” Cain said firmly. “Am I understood?”

 

“Yes,” Dean whispered. “Yes, Sir.”

 

“Good.”

 

The spanking continued until Dean felt real pain make his thighs and spine ache, but he held his tongue. He could _take_ it; he wasn’t a fucking pussy. Dean steeled himself, biting his tongue so hard it was close to bleeding when more hits were cracked across his bottom. Again, the spanking stopped for a moment and he felt Cain’s hands run up his back to his shoulders, helping him stand back up again.

 

Cain’s voice filled his ear soon after, speaking softly, “Dean, tell me if you are in real pain.”

 

Dean took a shuddering breath, wanting to push himself further, but he had a feeling that would be stupid. “Yeah. I need- I need a break.”

 

“There is no shame in that,” Cain told him gently, rubbing his hips and sides. “Go stretch out on the couch, we will care for you.”

 

Dean nodded as he walked over to lay down on his stomach, feeling his mood drop all the way to the basement. Tears were making it hard to see, so Dean buried his face in his arms, jerking when a hand began to rub and massage his back and shoulders. They were Benny’s hands; they were calloused, like Cain’s, but Cain’s hands were bigger. He sighed, trying not to sniffle or sob too loudly.

 

“Did real good, Sugar,” Benny praised him. “So good.”

 

Cain returned with the soothing lotion, slathering it on healthily, before he began to massage Dean’s legs, easing the cramps out of his calves and feet. Dean sighed, the tears still coming, but he could relax, going limp against the cushions. Benny pressed a kiss to Dean’s shoulder, and Dean held his breath, trying not to cry anymore. It was stupid, to cry; they’d been having fun and he was ruining it.

 

“I’m sorry I’m a bad sub,” he mumbled tiredly.

 

“Bad?” Benny asked, sounding shocked. “Dean, you ain’t _bad_. Sugar, you were fantastic.”

 

“Yes,” Cain echoed firmly. “Dean, what you’re experiencing is normal.”

 

He sniffed in response. “I don’t know what’s wrong with me,” he whimpered, allowing his tears to reach his voice this time.

 

“It’s called sub drop,” Cain said quietly. “It’s normal. It happens to most subs.”

 

“How do you make it stop?” Dean asked; he didn’t like feeling this way. It was awful, and if this was normal, he wasn’t sure he wanted to keep playing these games.

 

“Rest and care,” Cain told him, rubbing his calves again. “I will _always_ take care of you after, Dean. I can promise you that.”

 

“Wasn’t too bad for ya, was it?” Benny asked, sounding worried. Dean looked over at him and shook his head with a small smile. “Good.”

 

“Was it good for you?” he asked Benny, knowing it was good for Cain; he didn’t even have to ask.

 

“Oh, _yes_ , Sugar. Very good. I don’t know if Cain told ya, but I run a diner, and make _damn_ good pie. So, how about tomorrow, I bring ya some pie as a thank you, yeah? What’s your favorite flavor?” Benny continued to rub and pet him and Dean would have purred if he could have.

 

“Pecan,” he whispered.

 

“Pecan pie it is, Sugar.” Benny leaned in to give him a kiss. “But, I’ll get goin’, let you two have some privacy.”

 

“Thank you, Benny,” Cain said. “I’ll be right back Dean.”

 

Dean nodded and allowed Cain to walk Benny out, before he started to shift, attempting to sit up, but his behind told him _no_ , so he returned to lying on his stomach. Sitting in class was going to be s _o_ fun.

 

* * *

 

“What’s with the pillow?” Charlie asked him as she sat next to him in their lit class.

 

“Sore,” Dean muttered, feeling his face turn red, but he continued to stare at his laptop’s screen.

 

“Do I want to know?” she asked.

 

“Probably not.”

 

“Cool. You got work study today?”

 

He nodded. “Yeah, in the kitchens. They transferred me after I told that one kid to suck my left nut when he ripped up some library books right in front of me.”

 

Charlie snorted and nodded. “Serves him right.”

 

“Yeah, fuckin’ freshman.”

 

“Dude, we were ‘fuckin’ freshman’ a few weeks ago. Slow your roll.”

 

Dean rolled his eyes and continued to surf the internet, not caring to pay attention to class today. He’d already finished the book, and felt confident enough that he’d pass any exam their professor decided to throw at him.

 

“So, where you been anyway? Never see you around at video game club.” Charlie pouted, leaning toward him to see what he was doing, but Dean turned his computer from her. “Okay, okay, I get it. Jeeze. Get the stick outta your ass, Winchester.”

 

“Sorry,” he said with an apologetic smile. “I’ve been staying with a guy.”

 

She gasped, immediately intrigued. “A _guy_? Who? What’s his name? What’s he look like? Tell me.”

 

Dean snorted and bit his lip,glancing all around; no one was listening as far as he could tell. “I’m sorta… hooked up with an older dude… I’m like his… sugar baby, basically.” Charlie’s jaw dropped and Dean blushed. “Yeah.”

 

“Holy _shit_ ,” she gasped. “Damn, look at you, knowing how to get it. He nice to you?”

 

“Very nice.” Dean nodded and glanced at his computer again; he’d been reading about Cain’s company. He was head of some honey company, which did _not_ surprise Dean at all. The guy was head over heels for bees after all. He oversaw tons of bee farms.

 

“That him?” Charlie asked, managing to glance at his computer screen. “ _Damn_ , that’s a foxy dudebro.”

 

“He’s nice,” Dean repeated, smiling a little at Cain’s portrait; he did look quite refined and handsome in the photo. Dean immediately imagined being on his knees beneath Cain’s desk, giving him head during an important phone call.

 

“Yeah, you said that. He buy you presents?”

 

Dean gestured at the computer. “You think I pulled this outta my ass?” he laughed.

 

“Oh, right, no shit. _Duh_. New jacket, too?” she asked, gesturing at his coat.

 

“Yep.”

 

“Damn, sign me up.”

 

“Charlie, you're a lesbian.”

 

“Well, _duh_ , sign me up for the female version of this deal. I want to get shit in exchange for sexual favors.” Charlie smiled and nudged Dean’s ribs playfully. “But still, just because you’re doing some older guy doesn’t mean you can’t come mingle with the peasants, ya feel?”

 

He nodded with an embarrassed glance. “I know, I’m gonna talk to him about getting my social life back, I’ve been feeling kinda lonely up in the penthouse all day.”

 

“ _Shit_ , a penthouse and everything?” Charlie snorted. “Dude, I changed my mind, _don’t_ leave.”

 

“It’s not so bad, it’s just, I don’t have any friends up there, and I feel like I’m losin’ the ones I _do_ go, because I’m never down here on campus… Plus, my grades are slipping really bad. I gotta go to the tutoring session this afternoon.” He hated that he needed tutoring; it was embarrassing as hell.

 

Charlie smirked. “Yeah, less sex more studying.” She wagged her finger at him, but he couldn’t get a reply in because class had started, and he realized sadly, he really _should_ pay attention. Just in case.

 

* * *

 

Dean went to work study, tired, and still sore as hell. He had no desire to wash dishes, but work study helped pay his tuition bill. He was in the process of putting his stuff in the back room, when his supervisor approached him. “What’s up Bobby?” he said with a smile.

 

“Billing and HR want to see you, pronto,” Bobby said.

 

“What? Why?” Dean asked, sliding his coat back on and grabbing his bag.

 

“Dunno. Don’t think you’ll be back here though.”

 

That made Dean worry. He patted Bobby on the shoulder and took off toward HR’s office. Why the fuck wouldn’t he be back in the kitchens? He _needed_ work study, it was keeping him from being told to get the fuck out. The office was busy, but Dean approached the desk anyway, waiting to be noticed.

 

“Can I help you?” a brunette woman asked, looking as if she wanted another job, _any_ other job, than the one she had.

 

“I was told I was wanted-,” Dean cut off when someone ran into him, “Down here.”

 

“Name?”

 

“Winchester. Dean.”

 

The woman, Dean saw her nametag read MEG, dug through some files and then she nodded. “Right. You’ve been removed from the work study list.”

 

“ _Why_? I _need_ work study to pay what I owe-.” Dean didn’t want to cause a scene, but he was close to breaking down. This was _not_ what he needed today.

 

“Your bill’s been paid for in full,” Meg replied with a shrug. “The guy tried to pay us for the next few years in advance, but they wouldn’t let him… Anyway, you’re good. Account balance of zero.”

 

Dean stared and he felt his body growing cold from shock; Cain had paid his _tuition_ bill? “Oh,” he managed to say before walking out like a deer caught in too bright headlights. When he made his way back outside, Dean dug out his phone, and called Cain, pacing a long line along the building.

 

“Ah, Dean, were your ears burning?” Cain asked.

 

“You _paid_ for my tuition?” he squeaked, his voice sounding strangled.

 

“I did.”

 

“ _Why_?”

 

“Because, your worry about where the money is going to come from, is ruining your time as a student,” Cain replied simply. “I do not want you to worry about the tuition bill, I will take care of it.”

 

“But- but- that’s like… I mean, I got half covered, but that’s, that’s still a lot of money not accounted for-.” Dean couldn’t help but stammer. “I need to sit down.”

 

“Dean.”

 

“No, no, this is unfair. I can never pay you back for this-.” Dean sat down on a bench, pressing his hands to his forehead for a moment.

 

“Dean.”

 

“I can’t accept this-.” His voice was breaking into unexplained tears.

 

“I do not expect you to pay me back. It is a gift.”

 

“It’s too big of a gift,” he insisted. “I was gonna pay it off-.”

 

“With my money,” Cain replied quietly, which made Dean break down further. “I know that is why you accepted the position to live with me. I will admit, it hurts to know I had to go to monetary compensation to make someone stay, but I am simply beating you to the next step. You may now use the money for something else.”

 

Dean covered his mouth with one of his hands as he held back sobs. “I’m sorry,” he gasped.

 

“For what?”

 

“For using you.”

 

Cain’s voice sounded as if he were smiling, but Dean knew it was tinged with bitterness. “I did not expect anything less… You have been far kinder than any other boy I’ve had.”

 

He angrily wiped his eyes and tried to calm down again. “Thank you. For everything.”

 

“This sounds like a good-bye,” Cain commented quietly.

 

“No! No, it’s not a good bye. Just a thank you.” Dean took in a deep breath and straightened up to standing carefully. “I gotta ask you something, since I got you on the phone.”

 

“Of course, Dean.”

 

“Um, I’ve been kinda lonely at the penthouse, and I was just wondering, if I could… hang out on campus more. Do the clubs I used to… stuff like that.” Dean bit his lip and started to walk around; he had no idea what to do now, since he had no job to go to.

 

“Yes.”

 

“Really? That’s it. Just,” Dean lowered his voice to match Cain’s, “ ‘Yes’.”

 

Cain chuckled. “I do not wish you to give up your life for me, Dean, I would never ask you that.”

 

“Cool… So, um,” Dean glanced around and saw he was mostly alone on the sidewalk, “you wanna fool around on the phone?”

 

“I have a meeting in a few minutes,” Cain replied with a smile. “Tonight if you wish to fool around, we may.”

 

“Okay.” Dean hefted out a little sigh. “Guess I gotta find something else to do now that I don’t gotta work… which is _weird_ , but again, thanks. I really appreciate it.”

 

“I know, Dean. Call your sister,” he suggested. “Make up.”

 

Dean rolled his eyes. “Yeah, okay. Bye, old man.”

 

“Good bye, Dean. I will see you tonight… If you need to stay out later than eleven, that is alright with me.”

 

“Really?” Dean asked, honestly surprised.

 

“Yes.”

 

“Sweet. Okay, thanks. I’ll be home by three at the latest, I swear this time. Bye.” Dean hung up and looked around, wondering what there was to do on campus now that he was free as a bird. In the end, Dean found himself in the library reading a book for pleasure, which he hadn’t done in years, but it was a damn good way to pass the time before his next class (it was also a great place to rest his sore butt). Before his next class, Dean received a phonecall from his mother, so he left the book behind, and made his way out of the library in a hurry to answer.

 

“Hey, Mom.”

 

“How the hell did you pay off over fifteen thousand dollars in one day?” Mary asked him, sounding annoyed and alarmed. “What did you do, Dean?”

 

“Oh… um, about that-.”

 

“Dean, did you do something illegal?”

 

“What? Ma, _no_.” Dean sighed, running a hand over his face. “I sorta have a new boyfriend.” _That_ was weird, he realized, calling Cain his boyfriend. “He’s rich.”

 

“And he just _paid_ for your tuition?” He did not blame her for sounding so skeptical.

 

“Yeah, Mom, he did.”

 

“Why? Why would a man pay for your tuition bill, Dean?”

 

“Because I’m sleeping with him, okay!?” He sighed, kicking a nearby trashcan in rage. “Look, I didn’t know how to tell you… so, I just didn’t. I’m sorry.”

 

“You’re a hooker?” she asked, sounding even more stunned.

 

“ _No_ … Mom, I’m not a _hooker_. Jesus.” He sighed, walking toward his next class. “I’m seeing a rich guy and he pays me to stay with him, okay? He’s a nice guy, he’s not a weirdo or a creep or whatever.”

 

“A man who pays for your company Dean, is a john, which makes you-.”

 

“ _Swear_ to God Mom, call me a hooker _one_ more time.” He hung up, not wanting to deal with it right now. He turned off his phone entirely and walked to class with his hand stuffed in his pockets. Clearly, this was why he hadn’t wanted to tell her at all, but he was not going to let his mother’s words sour his mood. Not when he had video game club tonight and when he returned home, he was going to give Cain the best _thank you_ show he could muster.

 

* * *

 

 “You bitches miss me?” Dean asked as he walked into the lounge where the videogame club liked to confer.

 

“Dean!” Charlie cried, jumping up to hug him, which he hugged her back with a warm squeeze. “Dude, _so_ glad you’re here. We can’t get passed this fucking mission on _The Last of Us._ ”

 

Dean grinned, walking over to plop down onto a beanbag chair. “Controller.” He held out his hand expectantly and Kevin passed it over. “Oh shit, this level _blows_.”

 

“You beat it yet?” Kevin asked.

 

“Yeah, last week,” he muttered as he focused on getting them through the level.

 

“Been playing without us, Winchester?” Kevin laughed, giving him a little shove. “Jerk.”

 

Dean laughed and shrugged, soon going back to business. “Get bored, that’s all.” He couldn’t tell the entire club about Cain, no fucking way.

 

“So, you going to the swim banquet?” Charlie asked him. She was on the girls’ swimming team. He looked over at her and nodded.

 

“Yeah, I gotta,” he said. “Sort of the rules. Coach is still pissed as shit at me, but I think if I keep being a good, little swimmer he’ll chill out.” Dean grinned when he finished the level, handing the controller back to Kevin with a triumphant smile. “Boom.”

 

Charlie grabbed his arm. “I gotta tell you something. C’mere.”

 

The guys gave them shit when they walked off to talk in private but he flipped them off on his way. “What’s up?” he asked, once they were alone.

 

“So, I knew I recognized your dude’s face before,” she whispered. “Cain Apidae, right?”

 

He nodded. “Yeah, how’d you know?”

 

“He goes to the swim banquets. He’s one of the big players with all of the money… He donated the pool that we got built a few years back,” she whispered. “I just… thought you should know… I think that’s where he picks guys up.”

 

Dean frowned and shifted a little. He hadn’t been expecting that at all. “Yeah, but he’s got me now,” he said with a quick shrug. “He won’t just ditch me for someone else.”

 

“I’m just telling you, okay? Didn’t want you caught off guard when your _man_ was at the banquet, schmoozing up the other guys.” Charlie patted his shoulder and left him to stare and start to doubt himself; what if Cain _did_ find someone better? Dean felt his stomach drop and he had a feeling he was going to have to prove himself _extra_ awesome to keep in Cain’s favor.

 

 


	7. Chapter 7

Dean returned just a little before midnight, unable to focus on anything but Cain and the swim banquet. Surprisingly, Cain was still awake, walking around in nothing but a loose robe, which was almost a deterrent from Dean’s mission of asking him about past banquets.

 

“You’re home,” Cain said, his eyes moving to the nearest clock. “Early, I’m surprised.”

 

Dean nodded, setting his bags down, and walking over to grasp onto the man’s broad shoulders and kiss him deeply. He teased his tongue along Cain’s bottom lip until he was given entrance; usually, Dean was not about having the power, but in the moment, he took control of their passionate kiss, ending it before he could lose his mind from lust.

 

“Thank you,” Dean gasped.

 

Cain smiled a little and nodded. “You are most welcome, Dean.”

 

“Now,  have to ask you something before I blow you.”

 

Cain’s eyebrows raised and he smirked, walking over to remove the screaming tea kettle from the burner. “Oh?”

 

“There’s a swim banquet coming up and a friend of mine said you go to them. Is that true? I don’t remember seeing you around last year.” Dean walked over to stand on the opposite side of the counter, staring at Cain’s back and shoulders. “Cain?”

 

Cain poured the hot water into a mug before setting the kettle aside and turning to face Dean, tea in hand. “I do attend the swim banquets,” he admitted.

 

“Why? To hook up?”

 

Cain had the grace to flush and glance down at his tea as he stirred it. “This is my favorite,” he said, which threw Dean off for a moment, “I always add a bit of honey, it makes it taste better. Helps me sleep.”

 

“ _Cain_.”

 

There was a heavy sigh. “Yes, Dean, I attend them to hook up and to donate to the team.”

 

“And you just _weren’t_ gonna tell me?” Dean asked, his arms crossing in anger. “ _Fantastic_.”

 

“It’s not as if I would have hooked up _this_ year, Dean. I was not even sure if I would be _going_ this year, I didn’t go last year.” Cain sipped his tea casually.

 

“Why not?”

 

“I had someone.”

 

“And now you have me.” Dean shook his head and turned to walk away, annoyed and fed up. “Jesus, what, do you go through guys like pairs of used underwear?!”

 

“Dean-.”

 

“Don’t talk to me.” He stormed up the steps and slammed the door to his room a little too hard, throwing the lock. If Cain was going to meet someone and replace him, _let_ him, it was clearly inevitable. “Fucking dick,” he growled to the empty space, glancing around the room.

 

Over the past month and a half, he’d been able to collect things and make the room more to his personal liking; car and movie posters, jerseys, random signs and knickknacks covered the walls, and his closet was slowly filling with clothes. The bed was no long plain, white sheets and duvet; it was now plaid sheets, and a maroon and plaid comforter, along with matching pillow cases. The PS4, his laptop, and a good stereo system completed the hook up. Dean sighed and sank onto the bed, putting his face in his hands.

 

A knock came on his door. “Dean,” Cain called. “Please, open the door.”

 

“I _said_ don’t talk to me!” he snapped back.

 

A pause where Dean thought, perhaps, Cain had walked away, before the man spoke again, “Dean, I do not wish to replace you.”

 

“Well, you track record _blows_ and says the opposite.” He didn’t get up to open the door; if they were going to talk, Dean would make the bastard do it through a closed door.

 

“I did not wish to replace any of them either,” Cain admitted quietly, “but they left… Moved on. It is why I’ve… resulted to _paying_ someone.”

 

Dean frowned, finally looking over at the door in surprise. “You sayin’ you didn’t pay anyone before me?”

 

“I bought gifts but never did I include a stipend.”

 

Finally, Dean stood up and walked over to open the door very slowly, giving Cain a skeptical glance over. “So… You’re not gonna schmooze up some new dude?”

 

“Of _course_ not,” Cain said firmly. “Not unless you _wanted_ a companion.”

 

Dean snorted and shook his head. “I ain’t a dog, man, you don’t gotta get me a pal.”

 

“I will attend the banquet, simply to donate. That is all.” Cain reached up to tweaked his nose playfully, making him blush. “I enjoy your company too much to bring in someone new.”

 

“Okay,” he muttered, finally relenting and leaning against the door. “Can I still… ya know…”

 

“Oh, I will never turn down a sexual favor from you.” Cain kissed him and Dean whimpered, stepping up against Cain’s chest, allowing the older man to wrap his arms around him.

 

“Right here?” he panted, his desire too strong to even bother leaving the hallway. Cain smirked his answer, so Dean dropped to his knees and parted the robe to lick at the soft cock, eagerly making it hard in his hand.

 

“ _Mmm_ , I suppose I should buy you gifts more often,” Cain muttered. “You being so thankful and all.”

 

Dean looked up through his lashes, smiling coyly. “Pay my tuition for the next two and a half years, old man, and you’ll never get rid of me. I’m like a cat.” He winked and wrapped his mouth around Cain to suck, stroking his length with two hands. He focused on the head of Cain’s cock, licking and sucking on it until he made his lover groan.

 

“ _Good_ , Dean,” Cain praised, running his hands through Dean’s hair.

 

Dean sighed happily through his nose, shutting his eyes, and allowing himself to grow lost in Cain’s scent and taste. He moaned and pulled Cain’s cock in a little deeper; he had yet to deepthroat, but he wanted to try. If there was ever a man to try it on, it was Cain; he’d never hurt Dean on purpose.

 

“Not too much, Dean,” Cain chided lightly. “Don’t want you to choke.”

 

Again, Dean looked up at Cain. It made his heart warm to know Cain didn’t want to choke or hurt him; he was such a caring man. Dean moaned in response, taking in more, just before _too_ much, and sucked hard. Cain grunted and tugged at Dean’s hair a little. He would have grinned, but since have a dick in his mouth was preventing that, Dean allowed his stomach to fill with amused butterflies.

 

“ _So_ good,” Cain growled. “Very, very good.”

 

The warm and fuzzies filled his entire being; praise really did arouse him. Dean groaned and felt his cock jerk as he came in his panties. He hadn’t been given permission, but he had a feeling that didn’t matter at the moment. Cain pulled Dean back and he looked up in question.

 

“About to come,” the older man said, his eyes full of lust.

 

Dean pulled all the way back, sitting on his knees patiently, stroking the thick cock. “Come on my face, Daddy,” he panted. Cain growled and came hard, all over Dean’s face; he shut his eyes and allowed Cain to give him a facial. It wasn’t until he was licking his lips and fluttering his eyes open that he realized what had come out of his mouth. “Oh fuck- I didn’t mean-.”

 

Cain held up his hand and ran his thumb along Dean’s cheek, before dragging it down to his lips; Dean latched on immediately, sucking the cum off. “Do not apologize. It’s alright.”

 

A blush filled Dean’s face and he slowly removed his mouth from Cain’s thumb. “I don’t know why I said that,” he whispered. “It’s not weird… is it?”

 

“No.”

 

“So, it doesn’t freak you out or anything?”

 

“ _No_.” Cain smiled and ran his fingers through more of the mess, allowing Dean to suck and lick it off his fingers. “You’re a very good boy, Dean. Good boys get rewarded.” Dean moaned in response. “What is it that my boy wants? What can Daddy do for his boy?”

 

Dean whined, feeling his cock grow hard all over again. “I want to be fingered.”

 

Cain nodded, offering his hand, which Dean took. “Such a special boy, you are.”

 

Dean flushed, following Cain back to Cain’s bedroom. He stripped quickly, only leaving the wet panties on, unsure if those were to stay on or not. Today was a pale, pink pair made of lace and sheer fabric. There was no hiding the mess at all. When Cain turned to face him, his eyes traveled down Dean’s body, drinking him in hungrily.

 

“Am I pretty?” Dean asked quietly, feeling his chest turn red and his nipples harden. The words were flying out of his mouth and he had _no_ idea where they were coming from.

 

“Beautiful.” Cain sat down on the bed, his back pressed against the headboard, and patted his lap. “Come here.”

 

Dean nodded and slunk over, crawling on his hands and knees up the bed, slowly straddling Cain’s lap. Cain’s hands slid down his sides to cup his ass over the panties, giving him a few spanks. He whimpered; they weren’t punishment spanks, they were playful, and they made Dean’s cock twitch.

 

“My boy wants fingered, hm?” Cain asked, his voice deeper than usual. Dean nodded and gasped when Cain’s fingers slid inside the fabric of the panties to rub at his fluttering rim. “Have to get you a plug soon, pretty boy.”

 

A- a plug?” Dean asked, still unsure about all of the dirty language; sure, he knew the basics about sex, but he’d never down an in depth search.

 

Cain nodded and smiled, kissing underneath Dean’s chin, nibbling at his Adam’s apple. “Keeps you stretched… and keeps my come in your pretty hole.”

 

Dean shivered. “I’d like that.”

 

“I know.” A pleased smile slithered across Cain’s face as he reached for a bottle of lube, lubing up the fingers that had been teasing his rim just seconds before. With his clean hand, Cain grabbed Dean’s panties and yanked the back down off of his ass, grabbing a cheek to hold it spread roughly. Dean gulped and allowed his body to rise up on his knees just enough to give Cain more room.

 

“Daddy, I’m so horny,” he whimpered, shutting his eyes, wishing his mouth would stop running; he sounded ridiculous to his own ears, but when the cool fingers touched and rubbed his rim, he could only moan and force his hands to stay away from his own cock.

 

“I know you are, pretty boy,” Cain muttered as he slid two fingers into Dean’s hole, feeling the velvety, warm walls, stretching him eagerly. “And so well behaved, haven’t even bothered to touch your cock once.”

 

He gasped and sank down further onto Cain’s fingers, rocking his hips a little. “Feels- _so_ good,” he whimpered. Dean’s eyes flew open when he felt a third finger ease its way into his stretched hole. He felt _full_ ; almost as full as when Cain fucked him.

 

“How’s that?” Cain asked, his voice never leaving its calm, quiet, collected tone. Dean nodded, his eyes shut tight. “Relax. You’re doing very well.”

 

Dean took a few deep breaths, finally relaxing back against Cain’s hand, letting his dom and lover guide and rock him. Cain’s fingers worked slowly, focusing on stretching him open, rather than pleasuring him at the moment. Dean had a feeling that would change soon.

 

“Very good.”

 

Dean whimpered and bit his lip, allowing his eyes to open, even as they filled with tears from being so pleasured. “I think I’m gonna come-.”

 

“Try and hold it,” Cain muttered. Dean was glad there was no _demand_ for him to hold back; Cain understood he was having a hard time controlling himself.

 

“Okay,” Dean replied, his voice strained. He turned his eyes up to the ceiling, trying to focus on something else, but Cain’s fingers were pressing deeper and deeper, until they pressed against Dean’s sweet spot. He cried out, and slapped the headboard, pressing his palms against it heavily. “Shit-.”

 

“Very good, Dean, very good.” Cain wrapped his free arm around Dean’s waist to hold him steady. Cain’s fingers stilled, just a steady pressure against his prostate, allowing Dean to grow used to the overwhelming pleasure.

 

Again, Dean took a few deep breaths, tears falling down his cheeks, dripping onto Cain’s robe. He whimpered when Cain started to rub the spot again; it was sending little pulses of pleasure, like electric shocks, through his entire body, but especially through his cock. It ached and dripped dangerously, turning red and hardening further; Dean felt as if he grew any harder, it would split under the pressure.

 

“Good, good,” Cain praised, speeding his fingers up and tightening his arm around Dean’s waist. “Good, Dean.”

 

Dean cried out loudly, slapping the headboard again, his toes curling hard, and his jaw clenching as he held back the orgasm. The dirty, wet noises filled Dean’s ears, only making his arousal more insistent. “ _Shit_ ,” he gasped, breathing hard, but he was still managing to hold on.

 

Cain sped up just a little more and then he said the words that made Dean almost whimper in agonized pleasure. “You may come, Dean.”

 

Dean cried out loudly, not needing any more prompting as he came against Cain’s stomach and chest. “Jesus Christ!” he yelled, arching back against Cain’s arm, riding the man’s fingers quickly. “Yes, yes, _shit_.”

 

Cain was grinning ear to ear, looking extremely proud. “Oh, _yes_ , there’s my good boy.”

 

Dean moaned, finally relaxing. “Stop, stop- Im-p-pala, stop,” he panted, feeling the pain of overstimulation. Cain removed his fingers, and allowed Dean to sag backward. “Holy _fucking_ shit.”

 

Cain kissed Dean’s chest and up his neck along his jawline. “I’m so proud of you, Dean. That was wonderful.”

 

Dean smiled, lifting his head for a kiss. “Thank you,” he whispered. “That was amazing.”

 

“Yes, it was,” Cain agreed with a nod. “How about a bath, hm? Clean you up?”

 

“That sounds _awesome_.” Dean grinned, allowing Cain to carry him bridal style to the bathroom, since quite frankly, Dean’s legs felt like jelly anyway. He was set on the counter, while Cain filled the tub; it was a walk in, and Dean had a feeling it was deep enough to sit in and submerge his entire body. “Dude, your bathroom is like _porn_. I could jerk off to this set up.”

 

Cain laughed, filling the tub with hot water. “Bubbles, hm?”

 

“ _Yes_. I love bubbles.”

 

“I am not surprised.” Cain chuckled and dumped a few beads into the bath, and soon the tub was full of rich bubbles. Dean grinned excitedly.

 

“Join me?” he asked as Cain helped him into the tub. Dean groaned, relaxing easily, his eyes shutting. The warm water slid over his aching body, easing the aches away, replacing the feeling with sleepiness. “Please?”

  
Cain didn’t have to be asked twice.

 

**Notes for the Chapter:**

> this chapter was just porn, oops


	8. Chapter 8

**Notes for the Chapter:**

> i have absolutely no concept of moderation

There was a large gift box waiting for him when he returned from class. It was the night of the swim banquet and Dean smiled at the box, eagerly untying the bow, and lifting the lid. Beneath tissue paper was a note and a new suit jacket.

 

_I had to guess your size, but I have a good eye. We can have it altered if need be, but I am sure it will do for tonight. I hope you enjoy it. - C_

 

Dean grinned and set the note aside, removing the coat from the box to hold it up to the light. It was a deep, _deep_ red, which Cain must have noted was Dean’s favorite color. It would look good on top of a black shirt and the dark wash jeans he had gotten the other day for the evening.

 

“Thank _you_ , Mr. Apidae,” Dean muttered as he stripped out of his clothes to take a shower. After the banquet, he and some of the guys were going over to The Mid after to party. He secretly hoped Cain would just _show_ up. While Dean dried off from the shower, he removed his phone to call Cain at work, digging around in his drawer to find a pair of panties to wear; he’d basically started wearing them exclusively.

 

“Mr. Apidae’s office,” greeted Ruby, Cain’s secretary.

 

“Hey Ruby, it’s Dean. Is he busy?” Dean asked, holding the phone between his shoulder and jaw as he danced around to pull on underwear.

 

Ruby paused, clicking around on her keyboard. “He’s in a meeting for the next thirty minutes. You want me to leave a message?”

 

“Yeah, tell him that I want to talk to him ASAP, okay? Thanks.” Dean hung up and set the phone on the bed, pulling the new jeans from the closet. He had a plan for tonight and he hoped Cain would go along with it, but Dean was _fairly_ certain he would, since it was fucking genius. Thirty minutes later, Cain called him back, and Dean answered with a grin. “I got an idea.”

 

“Dean, I’m at work,” Cain replied immediately, which made Dean snort.

 

“Not that kind of idea,” he said. “I was thinking of a way to make us work out.”

 

“I’m confused.”

 

“I mean-. Sorry. I’m not wording this well… I was _thinking_ that tonight, at the party, you could pick me up.” Dean smiled, feeling like a total genius, but Cain remained silent. “Isn’t that a good idea? You could pretend to pick me out of the herd. It’s normal for you, right? Then, after, my friends and I are going to the Mid, and you could just, _show_ up.”

 

Cain chuckled, catching on. “I see. Are you sure you wish to be out?”

 

“ _God_ yes,” Dean groaned as he laid on the bed, staring up at the ceiling. “I’m tired of not being able to talk about it. It’s annoying. Plus, my Mom knows, so it’s not like I have anyone else to hide from now.”

 

“Alright, sounds like a plan… Did you receive the gift I sent to the house?” Cain asked. Dean could hear a leather chair squeaking and he envisioned his lover shifting in his seat, looking so bad ass in the office.

 

“Yeah, I love the jacket. Thanks.” Dean rolled over onto his stomach, kicking his feet playfully; he felt like a teenage girl, but he couldn’t help it. “So, when can I visit you at work?”

 

“You may visit me at work after tonight goes by.”

 

“So, my plan _is_ awesome.” Dean laughed. “I’m a genius.”

 

Cain chuckled. “Yes, you are… Now prepare for the party my genius boy, I will be a tad late, I have some work to finish up.”

 

“Okay,” Dean said, trailing off to yawn. “Oops, sorry… See you tonight. Bye.”

 

“Good bye, Dean.”

 

The call ended and Dean jumped back up to finish dressing, putting on a little extra cologne. Once the plan was put into motion, they could be out in public together, and Dean wouldn’t fear being “found out”. In Dean’s opinion, it was an _excellent_ idea.

 

* * *

 

The hors d'oeuvres were absolutely worth looking like a pig, Dean figured, as he stuffed his mouth like a glutton he was. The banquet and party had been going on for forty-five minutes and still no sign of Cain. He was about to basically choke on the mini apple pies, when someone cleared their throat, and he spun around, his mouth stuffed like a chipmunk’s. He swallowed quickly when he saw it was Cain, a smirk filling his blue eyes.

 

“Excuse me, I couldn’t help but… notice you,” Cain said smoothly, his eyes running up and down Dean’s body. “I did not mean to interrupt your snacking.”

 

Dean wiped his mouth on a napkin whilst blushing, feeling stupid butterflies fill his stomach. “Nah man, it’s cool...  Um, I’m… Dean.”

 

Cain smiled wider and offered his hand. “Cain Apidae. I’ve heard you are a true talent on this team, Mr. Winchester.”

 

Dean’s eyebrows shot up, actually surprised. “Yeah? No shit… Sorry, um, my coach is kinda pissed at me, so I’m surprised he said anything nice about me.”

 

“I saw your performance at the last meet,” Cain commented lightly, stepping closer, so close Dean could smell him. It wasn’t fair. “You are _very_ talented.”

 

The way Cain kept his voice, quiet and sultry, Dean could easily see why the guys on the team were being romanced by him; if they hadn’t been together already, they would have been by the end of the evening for sure. He stepped even closer, talking quietly, “I can see why you charm the pants off of the guys here.”

 

Cain chuckled. “Yes,” he replied, picking up a piece of cheese, popping it in his mouth.

 

Dean’s eyes followed Cain’s tongue as it licked his lips and immediately he clenched; fuck, did he need Cain’s tongue shoved up his ass. “Dude, you’re gonna give me a boner, chill,” he hissed, but Cain looked even more amused.

 

“That is the whole point, Dean,” he muttered against Dean’s ear.

 

“‘Course it is,” he muttered with a roll of his eyes. “So, Mr. Apidae,” he said, louder this time, “you an alum?”

 

“No, but I’ve always taken a fine interest in the swim team here at this university,” Cain replied as he picked up another hors d'oeuvres. “I also take _special_ interest in the swimming stars.”

 

Dean blushed and glanced back at Cain shyly. “Yeah?” he asked. “That right?”

 

“Oh, yes.” Cain’s hand went to his shoulder, giving it a squeeze, leaning into mutter for his ears only. “I don’t normally move so fast on the boys I pick out, but I would very much love to take you to somewhere more… _private_.”

 

Dean shivered; if this were for show, it was definitely working. “S-sure,” he whispered.

 

“Good.” Cain slid his hand to Dean’s lower back, steering him through the crowd, which made several people stare. There, it was done, they were seen together. From the look on some of the faces, Dean knew they _knew_ , but he blushed and smiled the whole way anyway.

 

As soon as they were alone in the hall, Dean relaxed. “Fuck, man, I am so horny.”

 

Cain smiled and continued to walk him along. “I wasn’t kidding, Dean.”

 

“Oh-... Sweet. Okay, cool.” He grinned and followed Cain’s lead, pressing into an unlocked room, where Cain was quick to push him up into a corner, sealing their mouths in a hungry kiss. Dean groaned, wrapping his arms around Cain’s shoulders, digging his fingers into the soft, longer hair. “Shit,” he gasped when they separated for air.

 

Cain’s hands worked his button and zipper down, allowing Dean’s jeans to slip down his thighs. “Panties?” he said with a smirk, winking. “How lovely.”

 

He smiled and blushed, glad they were still playing the game. “Yes, that’s right, I love panties.” Dean slid the jacket off and set it aside on a chair, turning around to face the wall, pressing his butt out for show. “I’m a fuckin’ slut, Mr. Apidae.”

 

“Yes, I can see that,” Cain remarked. His hands reached up to grab Dean’s ass, giving the cheeks a firm squeeze. “How about I ease some of that fire down, hm?”

 

“ _Please_ , Mr. Apidae.”

 

“It will be my _utmost_ pleasure,” Cain growled as he knelt down, pulling the panties down Dean’s smooth thighs. “ _Mmm_ , a pretty hairless boy.”

 

Dean groaned, pressing his forehead to the wall when Cain’s tongue flicked against his hole tentatively. “Y-yeah, got a wax… recently,” he muttered. “Hurt like a bitch.”

 

“You look very beautiful,” Cain complimented as he continued to run his tongue along Dean’s rim. Dean sighed, clenching his hands into fists along the wall, digging his nails at the paint. “You seem rather… sensitive.”

 

“I _am_ ,” he gasped, spreading his legs a little wider to get a better stance. “Fuck…” Dean could feel his hole clenching, wanting to be full.

 

Cain smirked, keeping Dean’s cheeks spread, still licking lightly, until he finally began to press his tongue into Dean. The feeling was met with a gasp and Cain dipped further, swirling his tongue along, pulling back to press a finger in, rubbing Dean’s prostate playfully. Dean moaned and shuddered, his cock hard and dripping.

 

“May I touch myself, Mr. Apidae?” he panted, his fingers twitching.

 

“Yes.”

 

“ _Thank you_ ,” he gasped, sliding his hand down to work his cock quickly while Cain continued to lick and finger him. “This- how you… greet all your boys?” Cain chuckled and Dean could feel the vibrations going along his rim; he whined.

 

“It is how I will greet _you_ , Dean,” Cain replied darkly, adding a second finger to his exploration.

 

“ _Sweet_.” Dean felt his jaw clench as he grew close to orgasm, Cain having no mercy on his g spot. “Gonna _blow_.”

 

“You may come whenever you like.” Cain’s beard was scratching his thighs and Dean hoped he had stubble burn later.

 

“You asked for it,” Dean panted as he cried out and came, clenching along Cain’s fingers, coating the wall. “ _Yeah,_ yeah, fuck.”

 

Cain made a pleased noise before standing up, pulling Dean’s panties back up over his hips, tucking his softening, messy cock away. His teeth scraped along Dean’s earlobe and he pressed a kiss along the soft patch of skin behind his ear. “I will meet you at the club tonight.”

 

Dean nodded. “Okay,” he whispered, thighs shaking. “Thank you.”

 

“Thank _you_ ,” Cain replied and then he was walking out, leaving Dean to follow, a smile on his face.

 

When he returned to the main room, immediately he was confronted by Charlie. “Hey,” he said, hoping his pants didn’t stain.

 

“ _Dude_ ,” she said, grabbing his arm and pulling him away. “What the fuck was that about?”

 

“I wanted to be out.” Dean shrugged. “I was sick of hiding it, so we figured he could “pick me up” and then people would know. It wouldn’t matter anymore.”

 

“Oh,” Charlie said. “Smart.”

 

Dean grinned. “I know,” he said proudly, puffing out his chest. “It was my idea.”

 

“You going to the club after?” she asked.

 

“Yeah. You?”

 

“ _Oh,_ yeah. Finally asked out Gilda the other night, she’s my date.” Charlie glanced back at the beautiful brunette in a long, white dress; it was very elvish, Dean thought. Lord of the Rings esque.

 

“Hey, good for you,” he said with a nudge to her ribs. “That’s awesome.”

 

“ _Yeah_ it is,” Charlie agreed with a fond smile back at Gilda. “She eats pussy like it’s her job.”

 

Dean blushed and looked away promptly. “Okay, that’s enough of that subject, moving on.”

 

“Oh, c’mon Dean, it’s like the _one_ sex thing we can relate on,” she said, looking at him. “You still like chicks, right?”

 

“Yeah,” he said defensively. “I do.”

 

“Well, then you get it.”

 

“Yes, I do, but I don’t need to know about it either.” Dean snatched up a glass of water from a table to sip. He spotted Cain, talking to some higher ups at the college, making them smile and laugh. He smiled a little and felt a blush creep along his ears, making his body feel entirely too hot.

 

“You’re blushing,” Charlie informed him, as if he had no idea.

 

“I _know_. Go bother your girlfriend or somethin’,” he said, turning to go find some of the guys. They were all standing together, talking, and laughing. “Hey, guys.”

 

They all looked at him and didn’t say anything. Dean blinked, unsure of why they were all giving him the _stare_. He laughed nervously, trying to play it off, but then his teammates were turning and ignoring him.

 

“What?” he asked, drawing their attention again.

 

“You fall for Cain’s bullshit, too?” Adam asked, making Dean blink in confusion. “He’s a total bastard, I’d stay away from him if I were you.”

 

“Wait, why?” Dean asked, suddenly concerned.

 

Adam stepped closer to him, pulling Dean away from the others to talk. “He promise you shit?”

 

“Yeah… I guess?”

 

“He promise he’ll stay with you forever  and you’re the perfect one for him, all of that crap?” Adam asked, looking dead serious. Dean grew nervous. He nodded. “It’s bullshit, don’t believe a word he says. I was with him last year, he cut me loose after six months.”

 

Dean blinked. “Why?”

 

Adam shrugged. “He got bored, I guess. Guess you’re his new thing.”

 

“How’d you guys meet?”

 

“Here.” Adam gestured around the room. “Took me to the back room and fucked me until I was a sobbing mess, it was _good_. Look, I won’t deny that the guy is good in the sack, but he’s also full of shit. Bought me gifts, told me I was _good_ and _perfect_. Paid for my tuition, can you believe that shit? Then, just like that.” Adam snapped his fingers, startling Dean. “Cut loose, like I was trash.”

 

Dean frowned, glancing over at Cain, not wanting to believe that would happen to him. “Sounds unbelievable,” he muttered.

 

“Yeah, well, you better believe it,” Adam snapped. “I’m not the only one. Guy’s been through most of our team.”

 

_That_ made Dean’s blood run cold. “You’re serious?”

 

“Yep. Guy picks the new one _every_ year, because they don’t any better, but seriously Dean, stay away from him. He’s a liar and he’s manipulative as fuck.”

 

“He never… hurt you, did he?” Dean asked, wondering if Cain turned out to be an abusive asshole.

 

“Physically? Nah, not unless I wanted him to, but to be honest, I’m not sure if _I_ ever really wanted him to, you got me?” Adam shook his head and squeezed Dean’s shoulder. “Do yourself a favor, and leave him _now_. The gifts and money are nice, but not _that_ nice.”

 

Dean gulped, nodded, and tried to ease the nerves in his stomach, but he couldn’t. His knees felt weak and he had to sit down, feeling as if he were going to throw up. Dean’s eyes raked across the room until he saw Cain shaking hands with a group of men; his eyes narrowed and he glared.

 

Tonight. He’d find out the truth _tonight_.

 

* * *

 

The Mid was hopping with life and music, so much so that they almost didn’t get in, but Dean followed the others inside; he wasn’t technically old enough, but the guys had already sweet talked the bouncer to let him as long as he didn’t drink. They all knew that was not going to happen.

 

Dean stood off to the side, glaring at the dance floor, sipping on a drink that one of the guys had bought him, seething. His eyes eventually fell on Cain, who was standing on the opposite side of the club, leaning against the second story balcony. Dean watched the bastard smirk and raise his drink in cheers, but Dean just glared darkly.

 

Eventually, Cain joined him, walking over slowly. “You look angry,” he said in Dean’s ear, since the music was so loud.

 

“We need to talk,” he replied. “Now.”

 

“We are talking,” Cain pointed out.

 

Dean spun to face him, wanting to throw the drink in Cain’s face. “You lied to me,” he growled.

 

“I beg your pardon?”

 

“Adam told me about your little _game_ you like to play… You’ve been through the majority of the swim team, that true?” Dean watched Cain’s face shift, looking worried for just a moment, but  the mask returned just as quickly. “Is it?”

 

“I have slept with your teammates, yes,” Cain admitted.

 

“And you just cut ‘em loose after a while, that true too? They didn’t _leave_ you, you just got bored and let them go.” Dean continued to glare, having to hold back from punching Cain in the nose. “Well?!”

 

“Dean, let me explain-.”

 

Dean shook his head, horrified. “You’re a _lying_ bastard,” he growled, turning away again. “Fuck off.”

 

“Dean, _please_ , allow me to explain.” Cain touched his shoulder but Dean yanked away. “Yes, I did let them go, they didn't leave, but they were all different. They weren’t _you_.”

 

“I don’t believe you,” Dean replied coldly. “Once a liar, always a liar.” He turned back around and pushed Cain hard in the chest, making him spill his drink along the fancy suit. “Adam _told_ me what you did to him! And the others. You _paid_ their tuition too, gave them a sweet, little taste of what it’d be like to _be_ with you, but then you just let them go. Cut them off.”

 

“Dean-.” Cain tried to protest, but Dean cut him off.

 

“Shut up,” he snapped. “I won’t let you use me until I’m dried up too, _no_ way. Go fuck yourself, I want _nothing_ more to do with you.” Dean turned and stormed out of the club, prepared to go home and pack his things. He was sure _someone_ would let him crash until he got his living situation figured out again.

 

“Dean!” Cain called, but Dean ignored him, glad to disappear into the crowd. He didn’t notice the tears running down his face until he was outside and a stranger asked him if he was okay. Giving a nod, Dean crossed the street to find a cab to take him back home. _Not home. Not home._ Not _home._

 

“Dean! Wait!” Cain was walking across the street with him and Dean wanted to turn and shove him back _into_ the street, but then that’d be a felony and he’d go to jail if the bastard was hit by a car. “Dean, please, wait.”

 

“ _Why_?! Why should I wait?! Give me a _fucking_ reason!” he screamed, opening the door to the cab.

 

Cain came to stand near him. “Never once did I have any of the others move in with me,” Cain replied quietly. “Never once have I taken one of the others to the cabin or invited a friend over to enjoy you as much as I do.”

 

Dean did pause, glancing over at Cain with hurt skepticism. “Why should I believe you?” he asked, his voice cracking.

 

Cain shrugged. “You have no reason to believe me,” he admitted, “but it’s the _truth_ , Dean. My track record is not clean, I admit that much, but Dean, I _do_ care for you. Very much. I have no desire to cut you loose.”

 

“Yeah, and what four months from now, you change your mind?” Dean snapped.

 

“No,” Cain said firmly. He took a step closer, laying his hand tentatively over Dean’s along the door of the cab. “Please, let me take you home.”

 

Eventually, Dean allowed Cain to take his hand and the door shut, the cabbie growing fed up, and taking off to leave them alone on the sidewalk. He looked down at the ground, unsure how to feel. “I don’t trust you,” he whispered.

 

“And that is _my_ fault,” Cain said firmly, “and I am so sorry for that. I will do what I can to remedy that trust. If you let me.”

 

Dean took a deep breath and nodded. “I want new rules.”

 

“Anything.”

 

Dean pulled his hand away. “We don’t have sex,” he said coldly. “I can’t look at you, let alone let you touch me right now. I get to sleep with who I want because you’ve made me into a _fucking_ sex maniac… You let me come around or not. You don’t push. Those are my conditions.”

 

Cain visibly swallowed and Dean could see him growing nervous, but he relented a nod. “If that is what you wish.”

  
“It is,” he snapped. Dean glanced over at the club again, glad his hand was still stamped. “I’m going back in, don’t follow me.” He turned on his heel and crossed the street, leaving Cain to go home alone.

 


	9. Chapter 9

After four shots, Dean was feeling loose enough to grind on a girl he didn’t know and in turn allow a strange man to grind on him. It wasn’t long before the dance floor was just a giant chain, which Dean followed around laughing. He would forget about Cain and how the man had been using him; how everything he said was probably _lies_ and deceit.

 

“Wanna come back to my place?” the girl yelled over the music. “

 

Dean grinned and nodded. “Hell yeah! Um… what’s your name again?”

 

“Nicole!”

 

“Right. Sweet.” Dean’s smile widened as he followed Nicole out of the club to the sidewalk. “Where you live, Sweetheart?”

 

She pointed off in a general direction. “Over there. C’mon.” Nicole began to stumble away, so Dean followed her. They giggled and pawed at one another, grabbing butts, and pulling on hair playfully the entire way down the dark sidewalk. Dean knew he was hammered, but it felt good to be completely drunk. He wanted to forget about Cain, even though the tiny voice in the back of his head was making that almost impossible.

 

_He wouldn’t want you to fuck some random girl without his permission. What if she’s gonna mug you? You do look nice, like you have money. Not to mention the new bank card with your name on it is linked to an account with a bit of money in it… Man, you are so dead._

 

“Wow, talk about shady neighborhood,” he laughed, trying to make light of the dark houses and cracked sidewalks. There weren’t any street lights either, it was just dark, dank, and terrifying. “Why’s a pretty thing like you livin’ in this dump, anyway?”

 

“Cheap rent,” Nicole replied, continuing to pull him along. “Besides, my friends paid for my entry into the club anyway.”

 

“Oh, well, smart… I guess.” Dean could feel his brain attempting to sober up as they just kept walking. “You live in a house down here or is your home that minivan over there?” Dean tried to smile and laugh, but nerves were settling into his brain; she didn’t seem as drunk as she’d appeared to be earlier, and he had seen _way_ too many horror movies.

 

“Ha. Ha.” Nicole finally stopped in front of a house and pulled him up the porch. “I know it’s not much, but it’s mine. Okay?”

 

“Hey, it’s a house.” Dean smiled and kissed her again, which made her giggle as she fumbled to get her keys and unlock the door. He pinched her ass, only making her giggle more, and then they were both heading inside. It wasn’t until she had him pressed against a wall, on her knees, his dick in her mouth that his mind, once again, wandered to Cain, and what this meant.

 

_He lied to you and you’re feeling bad for screwing some other girl? C’mon. He said it was ok… No. That doesn’t matter. Screw him… Okay, don’t_ screw _him, screw him, just… fuck him- Wait-._

 

“You okay?” Nicole asked, sounding actually worried. “You looked a little pale.”

 

“I can’t, I’m sorry-.” Dean tried not to push her back, because pushing ladies was rude, but he eventually tucked himself away, boner killed, and then he was out the door and walking toward the more lit parts of the street. It would be stupid to call Cain and ask for a ride, but he wasn’t exactly looking forward to trekking across town so late either.  In the end, he called, but he was at least unhappy about it.

 

“I’ll be there, go back to the club to wait.”

 

“Don’t tell me what to do,” Dean mumbled, even as he was going to just exactly that.

 

“I will be there shortly, Dean.”

 

“Whatever.” He hung up, realizing he was petty and stupid, no matter which way he spun it. He didn’t want Cain to come and pick him up, but he also didn’t want to be alone all night either. He hated that he couldn’t even sleep with someone else, even though he was _angry_. “Fuck!” he yelled angrily up at the sky, walking back toward the club. Dean leaned against the wall in annoyance, wishing he were a smoker so he could find something to do.

 

It wasn’t long before a fancy car was pulling up to him, which wasn’t the normal car, but the window rolled down revealing Cain to be the driver. “Dean,” he called.

  
Dean glowered and walked over, slinging into the car with as much annoyance as possible. “Didn’t even know you could drive,” Dean snapped, even though he knew the comeback was stupid.

 

“I can,” Cain replied seriously. “Are you alright?”

 

“No,” he growled. “I had to call you as a last resort because I couldn't sleep with someone else! I couldn’t bring myself to do it, which is _stupid_.” Dean crossed his arms and began to pout.

 

Cain glanced at him, opened his mouth to speak, and then stopped. “I’m sorry, Dean.”

 

“You _should_ be, you ass!”

 

“No, I mean, I am sorry for lying to you. For hurting you.”

 

Tears were making his vision blurry. “Whatever.”

 

“I know you’re angry, you have _every_ right to be angry, and I should have been more honest with you… but the way I feel about you? That I have not faked or lied about,” Cain said firmly. “Not once.”

 

Dean wiped his eyes on the back of his hand, annoyed that he was crying at all. Cain didn’t deserve his tears. “I’m _so_ mad,” he growled, clenching his hands into fists. “You don’t deserve my forgiveness.”

 

“And I will not ask for it,” Cain replied. “But I would ask for another chance.”

 

Slowly, Dean looked over at Cain. He could feel his heart weighing heavily in his chest; part of him believed Cain and that he really did care about _him_ , but the rest of him didn’t want to believe. “I don’t know if I can give you one,” he admitted tiredly.

 

“I see.” Cain’s shoulders slumped and it took Dean a moment to realize they were in the parking garage beneath the building. “I… understand.”

 

“Fall Break is coming up soon… I’m going to go home… and when I come back I’ll give you my decision about us… and if there is an ‘us’.” Dean climbed out of the car. That was the end of the conversation.

 

xxx

 

No longer used to the squeaks of the old house, Dean stared up at the water stained ceiling in his bedroom while his mother and sister went about their morning routine. Dean could hear Sammy attempting to be quiet, but she’d never exactly been Miss. Graceful.

 

“ _Sam_ , your brother is trying to sleep,” Mary hissed, too loudly, after there was a loud thump and something fell on the floor.

 

“Sorry,” Sammy replied.

 

Dean snorted and huffed out a sigh. Coming home had been awkward; he’d only been back for twenty-four hours. They hadn’t mentioned Cain, him being a “hooker”, or the money. Dean was glad, but he could also feel how strangled the air felt and it was just awkward. Dean sighed and glanced over at the clock; not even seven in the morning. He rolled over and attempted to go back to sleep, but it was pointless, and eventually Dean gave up and made his way downstairs.

 

“Oh,” Mary said when he appeared in the kitchen doorway. “Did we wake you up? I’m sorry, honey…”

 

Dean shrugged and went to ruffle Sammy’s hair but stopped short. “I mess up your hair, you’ll kill me, won’t you?”

 

Sammy gave him a death glare. “ _Yes_. It took an hour to straighten,” she replied, tossing it over her shoulder. “Mess with it and I’ll shove this fork-.”

 

“Samantha,” Mary said sternly which made Dean snort.

 

“Don’t worry Ma, it’s fine.” Dean glanced over at Sammy and wondered if things would stop being awkward between them soon, too. He had meant to call and glaze things over, but he’d never done it, and now he was living the consequences. He hadn’t even gotten a _hug_ when he’d showed up.

 

“Breakfast, Dean?” his mother asked, even as she placed a plate of eggs, toast, and bacon in front of him.

 

“Thanks,” he said with a genuine smile, which she returned and ran her hand along his hair gently. He picked up a fork to start digging in, glancing at Sammy again. “Still pissed at me?” he whispered when their mother returned to the food.

 

“Yep,” was the quick and clipped reply. Dean sighed and realized he wasn’t hungry after all.

 

“I’m going for a walk,” he proclaimed, tossing his fork aside, and then he was going for his shoes and coat; did it matter that it was chilly and all he had on were his pajama bottoms and a thin t-shirt? Nope.

 

“Dean-,” his mother called, wanting to protest, but Dean was out the door before she could say anything.

 

He walked down the driveway, pulling the hood of his jacket low over his hand and shoving his hands into the pockets. By the time he returned on Sunday, he had to make a decision about him and Cain; he had _hoped_ that home would give him the distance he needed to think, but home was just as stifled as the apartment. More so, even; at least Cain gave him space, his mother was always there and Sam was just being a bitch.

 

Dean glared down at the ground and gave a rock a firm kick, watching it skid across the pavement of the road. _Just forgive him, I mean it’s not like he’s been_ mean _to you. So he lied about the guys, doesn’t mean he’s about to throw you to the curb. He’s trying to keep you, don’t you think if he was gonna throw you away that he’d just let you go and not even bother? Of course, if you forgive him, you give him permission to let him lie_ again _about something else._

 

_Don’t give him permission to lie to you again._

 

He shuddered and kicked the rock again once he caught up to it. The sky was still dark and Dean shivered at the chilly air; turning around and going home before he caught something was probably best. Not to mention the drivers were _nuts_ out here and he didn’t have anything on that would make him stick out in the dark. If he got hit by a car, his mother would raise him from the dead so she could kill him herself. Dean smirked at the thought and then turned to head back home.

 

Maybe after Sammy’s day of school ended, they could talk and get some of the awkward out of the way. He didn’t like fighting with her, it wasn’t fun for either of them. When Dean came to the end of the driveway, Sammy was going to the bus, so Dean waved but was ignored… or Sammy hadn’t seen him. He decided that that was what he’d believe. It was better than thinking he’d been ignored completely.

 

The sounds of his mother cleaning up in the kitchen greeted Dean as soon as he walked inside, suddenly feeling very tired. Maybe going back to bed would be smart, but before he went upstairs, Dean walked back out to the kitchen and decided to help his mother by drying the dishes. Just like he’d done as a child. She gave him a shy smile and he smiled a little in return. They continued on in silence for most of the dishes, but eventually, Dean broke the silence.

 

“Mom, I’m sorry I didn’t tell you about Cain,” he said carefully. “I’m sure that hurt your feelings.”

 

“It did,” she admitted, “But I did overreact and I’m _sorry_ … I was just worried about you, is all… It just… It’s not something I’m used to.” She paused to dry her hands. “Dean, I just want you to be safe, that’s all.”

 

“I know, Mom. Thanks.” He sighed and finished the last plate. “We’re not really… together right now. It's complicated, but I can handle it. Okay?”

 

She frowned, her head tilting. “What do you mean, Dean?”

 

“He lied about some stuff, but not about some other stuff… I don’t know, it’s confusing. I’m mad because I still like him… and I hate that I still like him.” Dean looked away, unsure of what else he could say to make the situation make sense to her and to himself.

 

“Dean.” Mary reached over to touch his shoulder, making him look her in the eye again. “Men who lie, tend to continue to lie… That being said, you need to know what is best for _you_. If you feel you can give this man another chance, then by all means, go ahead and take that gamble. If you’re unsure, then follow your gut. It’s usually not wrong.”

 

Dean nodded a little and gave his mother a firm hug. “Thanks, Mom,” he whispered. He blushed when she kissed his cheek and he could feel his heart warming. Affection was always the quickest way into his heart.

 

“I love you, Dean… And I want you and Sam to make up. So, after school.” She gave him the _warning_ look, so he nodded, holding up his hands in defense. “Understood?”

 

“Yes, yes. I got it.”

 

“Good.”

 

xxx

 

“Hey loser, we’re going shopping, get in the car,” Dean called over to Sammy when he spotted her leaving with her friends. He had to admit, Sam made a very beautiful girl, it was amazing.

 

Sammy startled and made her way over with a frown. When she turned to wave to her friends, they were all giggling and whispering to each other. Dean puffed out his chest and grinned, which only made Sammy roll her eyes in annoyance. “Did you seriously just make a Mean Girls reference?” Sammy asked as she slid into the car.

 

“Maybe.” He shrugged, winked at the girls still giggling over him, and drove off toward the mall. “Figure I should make it up to you, that’s all.”

 

Sammy looked over at him, clearly not believing that at all. “Uh huh.”

 

“I’m serious! Look, I don’t approve of you sleeping with guys because you’re only fifteen, but I also hate fighting with you, man- I mean… girl.” That made Sammy laugh, so Dean relaxed a bit. “You know, you’re a lot prettier as a girl, I shoulda just known from the get-go.”

 

“Shut up!” Sammy punched his arm, which still hurt a lot, but Dean didn’t show it. “My friends think you’re cute.”

 

“Yeah?” Dean waggled his eyebrows and grinned as wide as possible.

 

“They’re also fifteen, Dean.”

 

“Hey, I’m not about to sleep with them but nothing wrong with getting a little surge of pride when someone or multiple someones think you’re cute, yeah?” Dean looked over at her and continued to smile. “Come on, forgive me? Please? You gotta admit, I was in the right.”

 

“I wouldn’t have been so mad if you weren’t _drunk_ off your ass,” Sammy replied angrily. “You’re right, I shouldn’t have slept with that guy, but you didn’t have the right to come in drunk and ruin everything.”

 

“I shouldn’t have been drunk,” he agreed with a nod, “but Sam, I had to step in. You are not old enough nor are you mentally mature enough to have sex. I mean, you’re lucky you don’t _actually_ have the girl parts yet or I woulda beat that guy more. What if he’d gotten you pregnant? You know? I mean… Sammy, if you’re gonna have sex, you have to be mature enough to handle the consequences of having sex.”

 

Sammy shifted a little, clearly uncomfortable now. “Oh.”

 

“Yeah. _Oh_.” Dean pulled into a parking space outside of the food court. “Do you understand why I was so upset? I mean, the guy who was banging you was too old for you, first of all. Not to mention you’re… I mean I don’t want to say you’re not ready for sex, but until you can conceive of all of the consequences and be prepared to handle them, then you’re not. Period.”

 

Sammy looked over at him and nodded. “I know it was stupid,” she whispered. “I’m sorry I called you a drunk and got mad at you.”

 

“I’m sorry I was drunk at all.” He shrugged. “So… we good now?”

 

“Yeah. We’re good.”

 

“ _Awesome_. Now, c’mon, I got some money let’s go blow it on useless shit.” Dean grinned and hopped out of the car, which made Sammy giggle, and together they rushed into the mall.

 

xxx

 

Dean stared up at the ceiling in his bedroom watching the sunlight dapple and move across in various waves. He was to go home tomorrow and he had to make a decision. _Go with your gut_. That’s what his mother had said; he knew what his gut said, even if his mind was saying the exact opposite. Dean groaned, rolled over, and picked up his phone to call Cain, pouting at the nightstand beside his bed. The phone rang a few times before Cain’s voice finally answered.

 

“Dean.” He sounded surprised, which Dean supposed wasn’t that… well… surprising.

 

“Hey,” Dean replied gruffly.

 

“It’s nice to hear from you.”

 

He huffed. “You can have another chance.” Dean felt his lips purse and there was a long pause. So long, Dean wondered if the line had died. “Dude?”

 

“I’m here, Dean. I was just surprised. Pleasantly so.”

 

“Yeah… I just- I miss you,” Dean whispered. “I really do.”

 

“I miss you too, Dean.”

 

Dean blushed and buried his face into the pillows on his bed. Maybe his gut would be right. Maybe his gut would send him into happiness. _Or maybe it’ll fuck you over. Idiot_. “No more lies, Cain,” he said sternly.

 

“I know, Dean. None… You will be back soon?”

 

“Yeah, tomorrow,” he replied.

 

Cain’s smile was apparent through his tone. “Good. I look forward to it.”

 

“Bye, Cain.”

 

“Good bye, Dean. See you tomorrow.”

  
Dean sighed and hung up. Not knowing for sure if it would work out was making him feel uneasy, but that, he supposed, was what it was like to go with one’s gut. “Better be fucking worth it,” he mumbled to no one in particular.

 

**Notes for the Chapter:**

> this update is so bad i'm sorry, i'm so busy with school and so tired ugh


	10. Chapter 10

“Harder, harder!” Dean held onto Cain’s shoulders tightly as they fucked harder into the bed. “Harder, damn it!”

 

Cain grunted and pounded him harder until the only sound Dean could hear was the snapping of flesh on flesh. “I missed you-,” Cain growled into his ear, which only made Dean moan. The words were like electroshocks down his spine; affection always made him feel as if he were flying on cloud nine.

 

“I missed you too, you asshole,” Dean replied angrily, digging his nails into Cain’s back. “I hate you and I missed you and I want you to fuck me _harder_ , Daddy.”

 

Cain dug into the bed and sped up making the headboard hit the wall in a steady _thud, thud, thud_. Dean groaned and stared up at the ceiling, his eyes slowly fluttering shut as the heat in his stomach grew into a wildfire. He was going to come soon.

 

“Hard enough for you?” Cain growled, kissing his neck until a bruise was sucked along his skin. “Hm?!”

 

“Y-yes,” he whimpered. “Yes, Daddy- _yes_!” Dean screamed the final ‘yes’ to the ceiling as he came, spilling a thick load along Cain’s stomach. “Fuck!!”

 

Cain groaned and came shortly after, filling him until he felt warm and full. They both stilled slowly, breathing hard, and staring at one another in the aftermath. “Dean-.”

 

“If you apologize again, I’ll kick you,” he mumbled sleepily with a small smile. “I know you’re sorry… It’s okay.”

 

“It’s not,” Cain replied with another firm kiss. “I care for you, Dean, and I should have never hurt you that way.”

 

“I know and I know you’re sorry... “ Dean kissed Cain’s chin slowly and hungrily; if he were honest, he’d tell Cain that the _feeling_ he’d had was love. The reason he had been so angry was Cain, a man he’d fallen in love with, had hurt him. “I forgive you,” he whispered.

 

Cain smiled and kissed him again. “So, back to school soon, hm?”

 

“Yeah,” he sighed. “I don’t even know if I want to go back.” Dean and Cain both shifted, so they could cuddle side by side.

 

“Why not?” Cain asked, propped up on his elbow to talk. “Is it too hard?”

 

“It’s not that.” Dean shrugged and looked over at him with a smile. “I just… I don’t know, I just really want to quit. It’s stupid. I don’t even know why, I just-.” He sighed, but Cain nudged him, prompting to keep talking. “I don’t really want to go to school again. Maybe I’m spoiled on the pool here and us just… going places. Being together.”

 

“Dean, I cannot condone you dropping out of school simply because you want to eat dessert and be fucked all day.” Cain gave him a wink and Dean blushed. “However, I could understand taking a break from school. Figure out what you wish to do.”

 

“Seriously?” Dean blinked and stared at him in surprise.

 

“Yes,” Cain replied with a nod. “Dean, there’s nothing wrong with pausing to figure yourself out… I am happy to continue to pay for school or to not. That is up to you, it is _your_ life.”

 

“So…” Dean trailed off with a smirk. “What can we _do_ while I figure myself out, hm?”

 

Cain replied with a chuckle and a kiss.

 

xxx

 

“Mom, Mom I can’t- I can’t hear you.” Dean sighed and pulled the phone away from his ear. He didn’t need to hear her yelling at him for dropping out for the semester to take a break. Cain raised an eyebrow at him but Dean waved his hand in dismissal. Eventually, she called his name and he returned the phone to his ear. “Mom, I’m at the airport, I really need to go.”

 

“Dean, I do not approve of you going off across the ocean with a man!” Mary said, her voice sounding distressed.

 

“Mom, I am _going_ to Italy, I am going to have a _great_ time with Cain, and I am going to be happy. I just want to figure myself out, Mom. Okay? I have to go-.”

 

“Dean,” Mary replied darkly, so he paused. “I want you to be _safe_. You call me once you get over there, okay?”

 

“Mom, it’ll cost you a fortune-,” he tried to protest.

 

“I don’t care Dean, I have to know you’re safe. Alright?” His mother’s voice was wavering so he nodded and said he’d call her. “Thank you… I love you, Dean.”

 

“I know, Ma, me too.” Slowly, he hung up and reached over to grab onto Cain’s hand, which was still odd for the older man. Dean knew Cain wasn’t used to overt affection in public, but Dean could tell he was pleased. “So, what’s Italy like, anyway?”

 

“Warm this time of year,” Cain replied as they walked along. “I have a lovely home on coast, I think you’ll enjoy it.”

 

“Of course I will,” he said smartly. “Considering we’re gonna fuck all day, every day.”

 

Cain snorted and pressed his hand along Dean’s lowerback, guiding him through the gates. “Yes, I suppose we will be having much sex… however, Dean, I do expect you to do something somewhat productive while on break.”

 

“Like what?” he asked, looking over at Cain in question. “Get a job?” Dean laughed. “You want me to get a job and be your _strong_ , working boy?”

 

Cain chuckled and pinched Dean along his side playfully. “I _want_ you to figure out what you want to do with your life, Dean.”

 

“And what if I don’t?” Dean asked, turning to face Cain in annoyance. They were supposed to be boarding, but he was too annoyed now. “What if I can’t? You gonna throw me out? Toss me away?”

 

“No, Dean,” he replied quietly. “I know you are young, I do expect you to build Rome in a day… I just don’t want you to waste your life away either.”

 

“I won’t… God, you sound like my mother.” Dean rolled his eyes in the same motion as he turned to board the plane. They were in first class and alone; either Cain had gotten them on an unpopular flight or paid someone off to be alone. Dean smirked a little at the thought of fucking on the way over, but then he remembered he was supposed to be annoyed.

 

Cain grabbed his ass firmly making him startle and turn around. “Are you misbehaving?” Cain asked quietly, his voice barely above a growl. “Hm?”

 

“Maybe,” he replied snottily. “What are you gonna do, Old Man?”

 

Cain smirked and brought him close, their lips almost touching. “As soon as this plane is stable I’m going to give you one hell of a punishment, _boy_.”

 

“I dare you,” he replied with a smirk. “I don’t think you got the balls.”

 

Cain smirked. “We’ll see.”

 

xxx

 

He wriggled and glared at the plate of food that he’d ordered. Cain was eating and reading a newspaper, looking somewhat amused. Dean was _not_ amused. “I hate you,” he said darkly, even as he had to bite back a whine.

 

“What was that, Dean?” Cain asked.

 

“I hate you,” he said again, his voice louder. The plug vibrating in his ass rose in intensity, making Dean grit his teeth. “Ah- _shit_.”

 

Cain smirked, setting the remote teasingly within Dean’s reach. “Eat your food, Dean. It’s a long, _long_ flight.”

 

“Ass.”

 

“Keep it up.” The rustle of the newspaper’s page turning made Dean shudder.

 

He whined pathetically, starting to grind against the seat in desperation. He wanted to come; he wanted to come as hard as possible to make a huge mess, but Cain had told him he wasn’t allowed to come. “ _Daddy,_ ” he whined, which made Cain glance up from the newspaper; he hated the bastard for wearing attractive reading glasses.

 

“Hm?” Cain asked.

 

“I wanna come.” The admission came out as a pathetic whimper, which was embarrassing, but Dean couldn’t help it; he was close, so _damn_ close. “Please.”

 

Cain half smiled but it quickly cleared away for his dom mask. “No.”

 

“But-.”

 

“You haven’t _earned_ it. Mouthing off to your Daddy.” Cain tsked and shook his head, returning his eyes to the newspaper. “Bad boys don’t get to come.”

 

He had to withhold a kick in Cain’s direction, gritting his teeth a little harder. “I’m sorry,” he whispered. “I’m sorry I was bad-.”

 

“I don’t think you are.” Cain shook his head and continued to read, flipping the page intermittently. “But you will be.”

 

Dean whined and rocked back and forth. “Daddy, _please_ -.” There were tears forming in his eyes, the vibrator was up too high; it was close to, too much. “It hurts-.”

 

Cain shifted at that, glancing over at him. “Does it really hurt or…”

 

He nodded. “Yeah-” Dean gasped, leaning back in his seat, unable to eat, trying to focus his breathing.

 

“Dean…”

 

“Impala, okay? Please turn it off or let me finish-.” Dean watched as Cain reached to shut off the toy, easing it off slowly, not wanting to do it too abruptly. Dean relaxed as the pain ebbed away, but he wanted to come more than anything else. The seat beside him grew heavy with weight and when Dean opened his eyes, they came to look into Cain’s.

 

“Let me take it out,” Cain whispered, reaching to brush his fingers along Dean’s cheek.

 

“No, it’s okay now,” he replied tiredly.

 

“I didn’t mean to hurt you, Dean.”

 

“No, I know. I know.” He nodded and pressed up against Cain’s side. “Cuddle me, Daddy.”

 

“Gladly.”

 

xxx

 

“You sure you wanna take pictures of me like this?” Dean asked as his cheeks turned red watching the lens follow him on the bed. He was naked, flushed, and bent over to show off his ass.

 

“Oh, _yes_ ,” Cain replied with a smile. “You’re lovely like this.”

 

“I feel stupid,” he replied but he allowed Cain to snap a few photos. “So stupid.”

 

“You look lovely.”

 

The sound of the shutter made Dean’s body fill with goosebumps. “I look _dumb_.”

 

“No bad talk.” Cain set the camera aside and gave Dean’s ass a light swat. “Not around me.”

 

“Sorry- _ahhhh_ , shit!” He twisted and turned as Cain’s tongue darted along his hole. “Shit- _oh fuck_ -.”

 

Rimming was by far his favorite activity. Cain’s chuckle made him whimper and shiver, his body starting to shake from excitement. He had missed Cain’s tongue; Cain’s mouth; Cain’s hands; Cain’s everything. He had missed Cain. His dom, his Daddy, his world. He moaned and shut his eyes.

 

“I love you,” he gasped out, unable to stop himself. The rimming paused and Dean gulped. Had he fucked up? Probably.

 

“What?” Cain asked, his voice low and without emotion.

 

“I said- I said, I loved you.” He pressed his forehead to the pillows. “Was that stupid?”

 

The bed shifted and then Cain was there, having him sit up, cupping his face. “Do you mean that?”

 

“Yes,” Dean whispered. “I did. I’m sorry.”

 

“Do not apologize,” Cain said firmly. “I… I love you as well, Dean, I just- I didn’t want to upset you.”

 

He gulped and felt himself close to blubbering; it was stupid, but Dean couldn’t help it either. “I can’t believe I just said I love you, while you were licking my asshole.”

 

Cain chuckled and pulled him close. “That’s alright.”

 

He sighed and shut his eyes while wrapping his arms around Cain’s waist. “I _love_ you.”

 

“I love you, too. Very much.”

 

“I can be yours… forever?” Dean bit his lip at the thought, unsure if it were a good idea or not.

 

“You may be mine for as long as you like.” Cain’s arms squeezed him and Dean smiled at the warmth and love he could feel in the simple gesture.

 

“Thank you.”

 

 

**Notes for the Chapter:**

> Ah, I felt as if this needed to end here. It just felt right to me. I'm sure you guys will think it's too short and needs more, but I was starting to feel the end was coming, I'm sorry, I know there's much left in the end. But, they made up, they came to a resolution, so I'm happy with the end :)


End file.
